Merging Boron with Nitrogen–Oxygen Bonds: A Review on BON Heterocycles

Abstract

Cyclic boronate esters play important roles in organic synthesis, pharmacology, supramolecular chemistry and materials science owing to their stability in air and versatile reactivity. Most of these compounds contain a B–O–C linkage with an alkoxy- or carboxylate group bound to the boron atom (e.g. boronate-diol esters, MIDA boronates). Boron chelates comprising a B–O–N motif (BON heterocycles) are much less explored, although first representatives of this class were prepared in the early 1960s. In recent years, there has been a growing interest in BON heterocycles as new chemotypes for drug design. The exocyclic B–O–N linkage, which is readily formed under mild conditions, shows surprising hydrolytic and thermal resistance. This allows the formation of BON heterocycles to be used as click-type reactions for the preparation of bioconjugates and functionally modified polymers. We believe that BON heterocycles are promising yet underrated organoboron derivatives. This review summarizes the scattered information about known types of BON heterocycles, including their synthesis, reactivity and structural data. Available applications of BON heterocycles in materials science and medicinal chemistry, along with their prospects, are also discussed. The bibliography contains 289 references.

Graphic Abstract

This is a preview of subscription content, access via your institution.

Fig. 1
Fig. 2
Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Fig. 3
Fig. 4
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10
Scheme 11
Scheme 12
Fig. 5
Scheme 13
Scheme 14
Scheme 15
Scheme 16
Scheme 17
Scheme 18
Scheme 19
Scheme 20
Fig. 6
Scheme 21
Scheme 22
Scheme 23
Scheme 24
Scheme 25
Scheme 26
Scheme 27
Scheme 28
Scheme 29
Scheme 30
Scheme 31
Fig. 7
Scheme 32
Scheme 33
Scheme 34
Scheme 35
Scheme 36
Scheme 37
Scheme 38
Fig. 8
Fig. 9
Scheme 39
Scheme 40
Scheme 41
Scheme 42
Scheme 43
Scheme 44
Scheme 45
Scheme 46
Scheme 47
Fig. 10
Scheme 48
Scheme 49
Scheme 50
Fig. 11
Scheme 51
Scheme 52
Fig. 12
Scheme 53
Scheme 54
Scheme 55
Scheme 56
Scheme 57
Scheme 58
Scheme 59
Scheme 60
Scheme 61
Fig. 13
Scheme 62
Scheme 63
Scheme 64
Fig. 14
Scheme 65
Scheme 66
Scheme 67
Scheme 68.
Scheme 69
Fig. 15
Scheme 70
Scheme 71
Scheme 72
Scheme 73
Scheme 74
Scheme 75
Scheme 76
Scheme 77
Scheme 78
Scheme 79
Scheme 80
Scheme 81
Scheme 82
Fig. 16
Fig. 17
Scheme 83
Scheme 84
Scheme 85
Scheme 86
Scheme 87
Scheme 88
Scheme 89
Scheme 90
Scheme 91
Scheme 92
Scheme 93
Scheme 94
Scheme 95
Scheme 96
Scheme 97
Scheme 98
Scheme 99
Scheme 100
Scheme 101
Scheme 102
Scheme 103
Fig. 18
Scheme 104
Scheme 105
Fig. 19
Scheme 106
Scheme 107
Scheme 108
Scheme 109
Scheme 110
Scheme 111
Scheme 112
Scheme 113
Scheme 114
Scheme 115
Scheme 116
Scheme 117
Scheme 118
Scheme 119
Scheme 120
Scheme 121
Scheme 122
Scheme 123
Fig. 20

References

  1. 1.

    Fyfe JWB, Watson AJB (2017) Chem 3:31–55

    CAS  Article  Google Scholar 

  2. 2.

    Brothers PJ (2017) Elements 13:255–260

    CAS  Article  Google Scholar 

  3. 3.

    Fernandez E (ed) (2020) Advances in organoboron chemistry towards organic synthesis. Georg Thieme Verlag, Stuttgart, p 574

    Google Scholar 

  4. 4.

    Fernandez E, Whiting A (eds) (2015) Synthesis and application of organoboron compounds. Springer, Berlin, p 331

    Google Scholar 

  5. 5.

    Lennox AJJ, Lloyd-Jones GC (2014) Chem Soc Rev 43:412–443

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  6. 6.

    Tan J, Yudin AK (2018) Drug Discov Today Technol 29:51–60

    PubMed  Article  PubMed Central  Google Scholar 

  7. 7.

    Beletskaya IP, Alonso F, Tyurin V (2019) Coord Chem Rev 385:137–173

    CAS  Article  Google Scholar 

  8. 8.

    Cid J, Gulyas H, Carbo JJ, Fernandez E (2012) Chem Soc Rev 41:3558–3570

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  9. 9.

    Focante F, Mercandelli P, Sironi A, Resconi L (2006) Coord Chem Rev 250:170–188

    CAS  Article  Google Scholar 

  10. 10.

    Hall DG (2019) Chem Soc Rev 48:3475–3496

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  11. 11.

    Legare M-A, Pranckevicius C, Braunschweig H (2019) Chem Rev 119:8231–8261

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  12. 12.

    Sivaev IB, Bregadze VI (2014) Coord Chem Rev 270–271:75–88

    Article  CAS  Google Scholar 

  13. 13.

    Paradies J (2019) Coord Chem Rev 380:170–183

    CAS  Article  Google Scholar 

  14. 14.

    Lam J, Szkop KM, Mosaferi E, Stephan DW (2019) Chem Soc Rev 48:3592–3612

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  15. 15.

    Stephan DW (2016) Science 354:1248

    CAS  Article  Google Scholar 

  16. 16.

    Yang F, Zhu M, Zhang J, Zhou H (2018) MedChemComm 9:201–211

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  17. 17.

    Baker SJ, Tomsho JW, Benkovic SJ (2011) Chem Soc Rev 40:4279–4285

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  18. 18.

    Smoum R, Rubinstein A, Dembitsky VM, Srebnik M (2012) Chem Rev 112:4156–4220

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  19. 19.

    Pratik Ashwinbhai V, Rakesh P, Abhay D (2020) Recent Patents Anti-Cancer Drug Discov 15:1–20

    Google Scholar 

  20. 20.

    Trippier PC, McGuigan C (2010) MedChemComm 1:183–198

    CAS  Article  Google Scholar 

  21. 21.

    Nocentini A, Supuran CT, Winum J-Y (2018) Expert Opin Ther Pat 28:493–504

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  22. 22.

    Fernandes GFS, Denny WA, Dos Santos JL (2019) Eur J Med Chem 179:791–804

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  23. 23.

    Flores-Parra A, Contreras R (2000) Coord Chem Rev 196:85–124

    CAS  Article  Google Scholar 

  24. 24.

    Hu K, Yang Z, Zhang L, Xie L, Wang L, Xu H, Josephson L, Liang SH, Zhang M-R (2020) Coord Chem Rev 405:213139

    CAS  Article  Google Scholar 

  25. 25.

    Antonio JPM, Russo R, Carvalho CP, Cal PMSD, Gois PMP (2019) Chem Soc Rev 48:3513–3536

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  26. 26.

    James TD, Sandanayake Samankumara KRA, Shinkai S (1996) Angew Chem Int Ed 35:1911–1922

    CAS  Article  Google Scholar 

  27. 27.

    Das BC, Thapa P, Karki R, Schinke C, Das S, Kambhampati S, Banerjee SK, Van Veldhuizen P, Verma A, Weiss LM, Evans T (2013) Future Med Chem 5:653–676

    CAS  PubMed  PubMed Central  Article  Google Scholar 

  28. 28.

    Wang S, Chen L, Jangili P, Sharma A, Li W, Hou J-T, Qin C, Yoon J, Kim JS (2018) Coord Chem Rev 374:36–54

    CAS  Article  Google Scholar 

  29. 29.

    Boodts S, Fron E, Hofkens J, Dehaen W (2018) Coord Chem Rev 371:1–10

    CAS  Article  Google Scholar 

  30. 30.

    Li D, Zhang H, Wang Y (2013) Chem Soc Rev 42:8416–8433

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  31. 31.

    Hirai M, Tanaka N, Sakai M, Yamaguchi S (2019) Chem Rev 119:8291–8331

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  32. 32.

    Kubo Y, Nishiyabu R, James TD (2015) Chem Commun 51:2005–2020

    CAS  Article  Google Scholar 

  33. 33.

    Arzt M, Seidler C, Ng DYW, Weil T (2014) Chem Asian J 9:1994–2003

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  34. 34.

    Brooks WLA, Sumerlin BS (2016) Chem Rev 116:1375–1397

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  35. 35.

    Nishiyabu R, Kubo Y, James TD, Fossey JS (2011) Chem Commun 47:1124–1150

    CAS  Article  Google Scholar 

  36. 36.

    Mellerup SK, Wang S (2019) Chem Soc Rev 48:3537–3549

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  37. 37.

    El-Kaderi HM, Hunt JR, Mendoza-Cortes JL, Cote AP, Taylor RE, O’Keeffe M, Yaghi OM (2007) Science 316:268–272

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  38. 38.

    Hall DG (2011) Boronic acids. Preparation and applications in organic synthesis, medicine and materials. Wiley-VCH, Weinheim, p 701

    Google Scholar 

  39. 39.

    Adamczyk-Wozniak A, Cyranski MK, Zubrowska A, Sporzynski A (2009) J Organomet Chem 694:3533–3541

    CAS  Article  Google Scholar 

  40. 40.

    Weber L (2008) Coord Chem Rev 252:1–31

    CAS  Article  Google Scholar 

  41. 41.

    Wang BJ, Groziak MP (2016) Adv Heterocycl Chem 118:47–90

    CAS  Article  Google Scholar 

  42. 42.

    Groziak MP (2000) Chapter 1—boron heterocycles as platforms for building new bioactive agents. In: Gribble GW, Gilchrist TL (eds) Progress in heterocyclic chemistry. Elsevier, New York, pp 1–21

    Google Scholar 

  43. 43.

    McConnell CR, Liu S-Y (2019) Chem Soc Rev 48:3436–3453

    CAS  PubMed  PubMed Central  Article  Google Scholar 

  44. 44.

    Su Y, Kinjo R (2019) Chem Soc Rev 48:3613–3659

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  45. 45.

    Knapp DM, Gillis EP, Burke MD (2009) J Am Chem Soc 131:6961–6963

    CAS  PubMed  PubMed Central  Article  Google Scholar 

  46. 46.

    Lehmann JW, Blair DJ, Burke MD (2018) Nat Rev Chem 2:0115

    PubMed  PubMed Central  Article  CAS  Google Scholar 

  47. 47.

    Pir M, Agirbas H, Budak F, Ilter M (2016) Med Chem Res 25:1794–1812

    CAS  Article  Google Scholar 

  48. 48.

    Ahlenstiel E, Kliegel W, Rettig SJ, Trotter J (1993) Can J Chem 71:263–271

    CAS  Article  Google Scholar 

  49. 49.

    Braunschweig H, Krummenacher I, Mailänder L, Rauch F (2015) Chem Commun 51:14513–14515

    CAS  Article  Google Scholar 

  50. 50.

    Boghi M, Hall DG (2018) Org Biomol Chem 16:4849–4856

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  51. 51.

    Ghosh P, Bag SP, Suri B, Sur P (1998) Neoplasma 45:68–72

    CAS  PubMed  PubMed Central  Google Scholar 

  52. 52.

    Sur P, Ghosh P, Bag SP, Sur B, Chatterjee SN (1999) Chemotherapy (Basel) 45:360–369

    CAS  Article  Google Scholar 

  53. 53.

    Murmu N, Mitra S, Das M, Gomes A, Vedasiromoni JR, Ghosh M, Bhattacharya M, Ghosh P, Biswas J, Bhattacharya S, Sur P (2001) J Exp Clin Cancer Res 20:511–515

    CAS  PubMed  PubMed Central  Google Scholar 

  54. 54.

    Murmu N, Ghosh P, Gomes A, Mitra S, Das M, Besra SE, Majumdar J, Bhattacharya S, Sur P, Vedasiromoni JR (2002) J Exp Clin Cancer Res 21:351–356

    CAS  PubMed  PubMed Central  Google Scholar 

  55. 55.

    Kar T, Scheiner S, Roy AK (2015) J Phys Chem C 119:15541–15546

    CAS  Article  Google Scholar 

  56. 56.

    Tandon HC, Husain MM (2007) J Indian Chem Soc 84:83–87

    CAS  Google Scholar 

  57. 57.

    Kroner J, Noelle D, Noeth H, Winterstein W (1975) Chem Ber 108:3807–3830

    CAS  Article  Google Scholar 

  58. 58.

    Lawong A, Ball D (2012) J Mol Model 18:1661–1666

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  59. 59.

    Ma D-X, Ren F-D, Hu T-P, Ren J (2010) J Mol Struct Theochem 942:121–130

    CAS  Article  Google Scholar 

  60. 60.

    Riedel S, Straka M, Pyykko P (2008) J Mol Struct Theochem 860:128–136

    CAS  Article  Google Scholar 

  61. 61.

    Parida R, Nambiar SR, Reddy GN, Giri S (2020) PCCP 22:1923–1931

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  62. 62.

    Reddy GN, Parida R, Jena P, Jana M, Giri S (2019) ChemPhysChem 20:1607–1612

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  63. 63.

    Reddy GN, Giri S (2016) RSC Adv 6:47145–47150

    CAS  Article  Google Scholar 

  64. 64.

    Naaresh Reddy G, Parida R, Giri S (2017) Chem Commun 53:9942–9945

    CAS  Article  Google Scholar 

  65. 65.

    Murase T, Suto T, Suzuki H (2017) Chem Asian J 12:726–729

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  66. 66.

    Vo C-VT, Mitchell TA, Bode JW (2011) J Am Chem Soc 133:14082–14089

    CAS  PubMed  PubMed Central  Article  Google Scholar 

  67. 67.

    Noda H, Bode JW (2015) J Am Chem Soc 137:3958–3966

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  68. 68.

    Golovanov IS, Mazeina GS, Nelyubina YV, Novikov RA, Mazur AS, Britvin SN, Tartakovsky VA, Ioffe SL, Sukhorukov AYu (2018) J Org Chem 83:9756–9773

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  69. 69.

    Hashimoto T, Gálvez AO, Maruoka K (2015) J Am Chem Soc 137:16016–16019

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  70. 70.

    Lee CF, Diaz DB, Holownia A, Kaldas SJ, Liew SK, Garrett GE, Dudding T, Yudin AK (2018) Nature Chem 10:1062–1070

    CAS  Article  Google Scholar 

  71. 71.

    Shitov OP, Tartakovsky VA, Golovanov IS, Sukhorukov AYu, Ioffe SL (2017) Chem Asian J 12:2237–2244

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  72. 72.

    Morita N, Kono R, Fukui K, Miyazawa A, Masu H, Azumaya I, Ban S, Hashimoto Y, Okamoto I, Tamura O (2015) J Org Chem 80:4797–4802

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  73. 73.

    Silva PJ, Ramos MJ (2009) J Org Chem 74:6120–6129

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  74. 74.

    Chen G-Q, Kehr G, Daniliuc CG, Erker G (2016) Dalton Trans 45:6820–6823

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  75. 75.

    Mo Z, Kolychev EL, Rit A, Campos J, Niu H, Aldridge S (2015) J Am Chem Soc 137:12227–12230

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  76. 76.

    Voloshin YZ, Novikov VV, Nelyubina YV (2015) RSC Adv 5:72621–72637

    CAS  Article  Google Scholar 

  77. 77.

    Jansze SM, Severin K (2018) Acc Chem Res 51:2139–2147

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  78. 78.

    Voloshin Y, Belaya I, Krämer R (eds) (2017) Cage metal complexes: clathrochelates revisited. Springer International Publishing, Cham, p 467

    Google Scholar 

  79. 79.

    F. Tuerkyilmaz, G. Kehr, J. Li, C.G. Daniliuc, M. Tesch, A. Studer, G. Erker, Angew. Chem., Int. Ed., 55 (2016) 1470–1473.

  80. 80.

    Tao X, Tuerkyilmaz F, Daniliuc CG, Kehr G, Erker G (2017) J Organomet Chem 847:167–172

    CAS  Article  Google Scholar 

  81. 81.

    Paetzold P, Englert U, Finger R, Schmitz T, Tapper A, Ziembinski R (2004) Anorg Z Allg Chem 630:508–518

    CAS  Article  Google Scholar 

  82. 82.

    Yale HL, Bergeim FH, Sowinski FA, Bernstein J, Fried J (1962) J Am Chem Soc 84:688–689

    CAS  Article  Google Scholar 

  83. 83.

    Yale HL (1971) J Heterocycl Chem 8:205–208

    CAS  Article  Google Scholar 

  84. 84.

    Dürüst Y, Dürüst N, Akcan M (2007) J Chem Eng Data 52:718–720

    Article  CAS  Google Scholar 

  85. 85.

    Dornow A, Fischer K (1966) Chem Ber 99:68–71

    CAS  Article  Google Scholar 

  86. 86.

    Pailer M, Huemer H (1964) Monatsh Chem 95:373–378

    CAS  Article  Google Scholar 

  87. 87.

    Nigam L, Gupta VD, Mehrotra RC (1980) Synth React Inorg Met-Org Chem 10:491–507

    CAS  Article  Google Scholar 

  88. 88.

    Raper E (1978) Acta Cryst B 34:3281–3284

    Article  Google Scholar 

  89. 89.

    Cragg RH, Miller TJ (1982) J. Chem. Soc. Dalton Trans. 20:907–909

    Article  Google Scholar 

  90. 90.

    Moehrle H, Bluhme-Hensen K, Middelhauve B, Mootz D, Wunderlich H (1991) Z Naturforsch B 46:1219–1222

    CAS  Article  Google Scholar 

  91. 91.

    Moehrle H, Lessel J (1992a) Chem Ber 125:1843–1849

    CAS  Article  Google Scholar 

  92. 92.

    Moehrle H, Lessel J (1991) Arch Pharm (Weinheim Ger) 324:367–372

    CAS  Article  Google Scholar 

  93. 93.

    Das MK, Chakraborty S (1990a) Z Naturforsch B Chem Sci 45:1123–1127

    CAS  Article  Google Scholar 

  94. 94.

    Das MK, Chakraborty S (1990b) Indian J Chem Sect A 29A:352–355

    CAS  Google Scholar 

  95. 95.

    Goel AB, Gupta VD (1977) J Indian Chem Soc 54:581–585

    CAS  Google Scholar 

  96. 96.

    Goel AB, Gupta VD (1975) Bull Chem Soc Jpn 48:2997–2998

    CAS  Article  Google Scholar 

  97. 97.

    Goel AB, Gupta VD (1974) J Organomet Chem 77:183–188

    CAS  Article  Google Scholar 

  98. 98.

    Kobashi K, Terashima N, Hase J (1973) Chem Pharm Bull 21:2303–2308

    CAS  Article  Google Scholar 

  99. 99.

    Zinner G, Nebel G (1970) Arch Pharm. (Weinheim, Ger.) 303:385–390

    CAS  Article  Google Scholar 

  100. 100.

    Moehrle H, Lessel J (1992b) Arch Pharm. (Weinheim, Ger.) 325:23–27

    CAS  Article  Google Scholar 

  101. 101.

    Dürüst Y, Akcan M, Martiskainen O, Pihlaja K (2008) Polyhedron 27:999–1007

    Article  CAS  Google Scholar 

  102. 102.

    Lessel J, Herfs G (2000) Pharmazie 55:22–26

    CAS  PubMed  PubMed Central  Google Scholar 

  103. 103.

    Pilipecz MV, Varga TR, Králl P, Vincze Z, Mucsi Z, Deme R, Szabó PT, Nemes P (2020) Synth Commun 50:1712–1723

    CAS  Article  Google Scholar 

  104. 104.

    Adachi S, Liew SK, Lee CF, Lough A, He Z, Denis JDS, Poda G, Yudin AK (2015) Org Lett 17:5594–5597

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  105. 105.

    Paetzold PI, Stohr G (1968) Chem Ber 101:2874–2880

    CAS  Article  Google Scholar 

  106. 106.

    Doerksen RJ, Thakkar AJ (2002) Int J Quantum Chem 90:534–540

    CAS  Article  Google Scholar 

  107. 107.

    Pir M, Agirbas H (2018) J Struct Chem 59:949–954

    CAS  Article  Google Scholar 

  108. 108.

    Doerksen RJ, Thakkar AJ (1999) J Phys Chem A 103:2141–2151

    CAS  Article  Google Scholar 

  109. 109.

    Meunier-Piret J, Piret P, Germain G, Putzeys J-P, Van Meerssche M (1972) Acta Cryst B 28:1308–1311

    CAS  Article  Google Scholar 

  110. 110.

    Kuribayashi S (1973) Bull Chem Soc Jpn 46:1045–1048

    CAS  Article  Google Scholar 

  111. 111.

    Bullen GJ (1973) J Chem Soc Dalton Trans 20:858–863

    Article  Google Scholar 

  112. 112.

    Rettig SJ, Trotter J (1974) Acta Cryst B 30:2139–2145

    Article  Google Scholar 

  113. 113.

    Macháček J, Bühl M, Fanfrlík J, Hnyk D (2017) J Phys Chem A 121:9631–9637

    PubMed  Article  CAS  Google Scholar 

  114. 114.

    Settepani JA, Stokes JB, Borkovec AB (1970) J Med Chem 13:128–131

    CAS  PubMed  Article  Google Scholar 

  115. 115.

    Borkovec AB, Settepani JA, LaBrecque GC, Fye RL (1969) J Econ Entomol 62:1472–1480

    CAS  PubMed  Article  Google Scholar 

  116. 116.

    Bag SP, Ghosh P, Sur B, Sur P (1998) J Indian Chem Soc 75:313–314

    CAS  Google Scholar 

  117. 117.

    Moehrle H, Lessel J (1992c) Pharmazie 47:243–245

    CAS  Google Scholar 

  118. 118.

    Moehrle H, Lessel J (1990) Arch Pharm (Weinheim, Ger) 323:915–918

    CAS  Article  Google Scholar 

  119. 119.

    Brauer DJ, Bürger H, Pawelke G, Rothe J (1996) J Organomet Chem 522:129–136

    CAS  Article  Google Scholar 

  120. 120.

    Paetzold P, Truppat R (1983) Chem Ber 116:1531–1539

    CAS  Article  Google Scholar 

  121. 121.

    Paetzold P, Schroeder E, Schmid G, Boese R (1985) Chem Ber 118:3205–3216

    CAS  Article  Google Scholar 

  122. 122.

    Paetzold P, Schimmel G (1980) Z Naturforsch B Anorg Chem Org Chem 35B:568–577

    CAS  Google Scholar 

  123. 123.

    Ito M, Tokitoh N, Okazaki R (1997) Tetrahedron Lett 38:4451–4454

    CAS  Article  Google Scholar 

  124. 124.

    Umland F, Schleyerbach C (1965) Angew Chem Int Ed 4:151–151

    Article  Google Scholar 

  125. 125.

    Hohaus E, Riepe W (1976) Z Naturforsch B Anorg Chem Org Chem 31B:324–329

    CAS  Google Scholar 

  126. 126.

    Rettig SJ, Trotter J, Kliegel W, Nanninga D (1978) Can J Chem 56:1676–1680

    CAS  Article  Google Scholar 

  127. 127.

    Kliegel W, Nanninga D (1983a) Pharmazie 38:131–132

    CAS  Google Scholar 

  128. 128.

    Kliegel W, Schumacher U, Tajerbashi M, Rettig SJ, Trotter J (1991) Can J Chem 69:545–549

    CAS  Article  Google Scholar 

  129. 129.

    Kliegel W, Tajerbashi M, Rettig SJ, Trotter J (1990) Can J Chem 68:69–73

    CAS  Article  Google Scholar 

  130. 130.

    Kliegel W, Metge J, Patrick BO, Rettig SJ, Trotter J (2001) Acta Cryst E 57:o1120–o1122

    CAS  Article  Google Scholar 

  131. 131.

    Kliegel W, Schumacher U, Patrick BO, Rettig SJ, Trotter J (2002a) Acta Cryst E 58:o1215–o1217

    CAS  Article  Google Scholar 

  132. 132.

    Kliegel W, Schumacher U, Patrick BO, Rettig SJ, Trotter J (2002b) Acta Cryst E 58:o1095–o1097

    CAS  Article  Google Scholar 

  133. 133.

    Kliegel W, Nanninga D (1983b) Chem Ber 116:2616–2629

    CAS  Article  Google Scholar 

  134. 134.

    Kliegel W, Nanninga D, Rettig SJ, Trotter J (1983a) Can J Chem 61:2493–2499

    CAS  Article  Google Scholar 

  135. 135.

    Bessler KE, Dourado EB, Carvalho MDS, Lemos SS, Ellena J (2005) Z Anorg Allg Chem 631:1935–1940

    CAS  Article  Google Scholar 

  136. 136.

    Das MK, Biswas B, Chakraborty S, Noth H, Pidcock A (1986) Synth React Inorg Met-Org Chem 16:77–84

    CAS  Article  Google Scholar 

  137. 137.

    Stolowitz ML, Ahlem C, Hughes KA, Kaiser RJ, Kesicki EA, Li G, Lund KP, Torkelson SM, Wiley JP (2001) Bioconjugate Chem 12:229–239

    CAS  Article  Google Scholar 

  138. 138.

    Martínez-Aguirre MA, Flores-Alamo M, Yatsimirsky AK (2018) Appl Organomet Chem 32:e4405

    Article  CAS  Google Scholar 

  139. 139.

    Umland F, Hohaus E, Brodte K (1973) Chem Ber 106:2427–2437

    CAS  Article  Google Scholar 

  140. 140.

    Rettig SJ, Trotter J, Kliegel W, Nanninga D (1977) Can J Chem 55:1–7

    CAS  Article  Google Scholar 

  141. 141.

    Mukhopadhyay D, Sur B, Bhattacharyya RG (1981) J Inorg Nucl Chem 43:607–609

    CAS  Article  Google Scholar 

  142. 142.

    Kliegel W, Tajerbashi M, Rettig SJ, Trotter J (1991) Can J Chem 69:673–680

    CAS  Article  Google Scholar 

  143. 143.

    Zhang W, Li F, Bian Z, Lou M (1995) Neimenggu Daxue Xuebao Ziran Kexueban 26:571–574

    CAS  Google Scholar 

  144. 144.

    Prabhakar S, Lobo AM, Tavares MR (1978) J Chem Soc Chem Commun 20:884–885

    Article  Google Scholar 

  145. 145.

    Pereira MMA, Prabhakar S, Lobo AM (1996) J Nat Prod 59:744–747

    CAS  PubMed  Article  Google Scholar 

  146. 146.

    Prabhakar S, Lobo AM, Marques MM, Tavares MR (1985) J Chem Res Synop 30:394–395

    Google Scholar 

  147. 147.

    Matsumoto M, Wada K, Urakawa K, Ishikawa H (2020) Org Lett 22:781–785

    CAS  PubMed  Article  Google Scholar 

  148. 148.

    Ye KY, Kehr G, Daniliuc CG, Liu L, Grimme S, Erker G (2016) Angew Chem Int Ed 55:9216–9219

    CAS  Article  Google Scholar 

  149. 149.

    Das MK, Chakraborty S (1988) Synth React Inorg Met-Org Chem 18:225–230

    CAS  Article  Google Scholar 

  150. 150.

    Reilly, U., Melnick, M. J., Brown, M. F., Plummer, M. S., Montgomery, J. I., Che, Y., Price, L. M., Johnson, T. A., Ewin, R. A., Uccello, D. & Braish, T. F. (Pfizer Inc.); Patent WO 2019175828, A1, Sept. 19 (2019).

  151. 151.

    Bessler E, DeflonVictor M, Weidlein J (1993) Z Naturforsch B 48:1275–1278

    CAS  Article  Google Scholar 

  152. 152.

    de Figueiredo AT, Deflon VM, Bessler KE, Maichle-Mössmer C, Abram U (2002) Polyhedron 21:2351–2356

    Article  Google Scholar 

  153. 153.

    Lamande L, Boyer D, Munoz A (1987) J Organomet Chem 329:1–29

    CAS  Article  Google Scholar 

  154. 154.

    van Haveren J, van den Burg MHB, Peters JA, Batelaan JG, Kieboom APG, van Bekkum H (1991) J Chem Soc Perkin Trans 2:321–327

    Article  Google Scholar 

  155. 155.

    Denis P, Ventura ON (2001) J Mol Struc-Theochem 537:173–180

    CAS  Article  Google Scholar 

  156. 156.

    Brown, M. F., Che, Y., Marfat, A., Melnick, M. J., Montgomery, J. I., Johnson, T. A., Ewin, R. A., Uccello, D., Reilley, U., & Braish, T. F. (Pfizer Inc.); Patent WO 2019178305, A1, Sept. 19 (2019).

  157. 157.

    Kliegel W, Schumacher U, Rettig SJ, Trotter J (1996) Can J Chem 74:445–452

    CAS  Article  Google Scholar 

  158. 158.

    Rettig SJ, Trotter J, Kliegel W (1974) Can J Chem 52:2531–2541

    CAS  Article  Google Scholar 

  159. 159.

    Kliegel W, Amt H, Patrick BO, Rettig SJ, Trotter J (2002) Acta Cryst E 58:o473–o475

    CAS  Article  Google Scholar 

  160. 160.

    Kliegel W, Motzkus HW, Rettig SJ, Trotter J (1984) Can J Chem 62:838–844

    CAS  Article  Google Scholar 

  161. 161.

    Graumann J, Kliegel W (1982) Chem-Ztg 106:345–347

    CAS  Google Scholar 

  162. 162.

    Kliegel W (1969a) Z Chem 9:112–113

    CAS  Article  Google Scholar 

  163. 163.

    Zinner G, Ritter AW (1962) Angew Chem 74:217–217

    CAS  Article  Google Scholar 

  164. 164.

    Zinner G, Moderhack D, Kliegel W (1969) Chem Ber 102:2536–2546

    CAS  PubMed  Article  Google Scholar 

  165. 165.

    Kliegel W, Riebe U, Rettig SJ, Trotter J (1995) Can J Chem 73:835–845

    CAS  Article  Google Scholar 

  166. 166.

    Kliegel W, Riebe U, Rettig SJ, Trotter J (1998) Can J Chem 76:1789–1795

    CAS  Article  Google Scholar 

  167. 167.

    Magnus P, Gazzard L, Hobson L, Payne AH, Rainey TJ, Westlund N, Lynch V (2002) Tetrahedron 58:3423–3443

    CAS  Article  Google Scholar 

  168. 168.

    Magnus P, Hobson LA, Westlund N, Lynch V (2001) Tetrahedron Lett 42:993–997

    CAS  Article  Google Scholar 

  169. 169.

    Kliegel W, Druckler K, Patrick BO, Rettig SJ, Trotter J (2002) Acta Cryst E 58:o393–o395

    CAS  Article  Google Scholar 

  170. 170.

    Shitov O, Leont’eva L, Ioffe S, Khasapov B, Novikov V, Stepanyants A, Tartakovskii V (1974) Russ Chem Bull 23:2684–2691 ((CAS Accession Number: 1975:125430. Shitov O, Leont’eva L, Ioffe S, Khasapov B, Novikov V, Stepanyants A, Tartakovskii V (1974) Izv Akad Nauk SSSR Ser Khim 23:2782–2790 (in Russian))

    Article  Google Scholar 

  171. 171.

    Kliegel W, Nanninga D, Rettig SJ, Trotter J (1983b) Can J Chem 61:2329–2333

    CAS  Article  Google Scholar 

  172. 172.

    Kliegel W (1983) J Organomet Chem 253:9–16

    CAS  Article  Google Scholar 

  173. 173.

    Kliegel W, Rettig SJ, Trotter J (1984) Can J Chem 62:515–520

    CAS  Article  Google Scholar 

  174. 174.

    Loetz A, Voitlaender J, Stephenson D, Smith JAS (1986) Z Naturforsch A Phys Phys Chem Kosmophys 41A:200–202

    CAS  Google Scholar 

  175. 175.

    Kliegel W, Lubkowitz G, Rettig SJ, Trotter J (1992a) Can J Chem 70:2022–2026

    CAS  Article  Google Scholar 

  176. 176.

    Kliegel W, Lubkowitz G, Rettig SJ, Trotter J (1992b) Can J Chem 70:2015–2021

    CAS  Article  Google Scholar 

  177. 177.

    Friese B, Umland F (1978) Anal Chim Acta 96:303–310

    CAS  Article  Google Scholar 

  178. 178.

    Neu R, Anal Z (1960) Chem Freseniu 176:343–346

    CAS  Article  Google Scholar 

  179. 179.

    Amt H, Kliegel W, Rettig SJ, Trotter J (1990a) Can J Chem 68:1791–1796

    CAS  Article  Google Scholar 

  180. 180.

    Amt H, Kliegel W, Rettig SJ, Trotter J (1988) Can J Chem 66:1117–1122

    CAS  Article  Google Scholar 

  181. 181.

    Kliegel W, Lubkowitz G, Rettig SJ, Trotter J (1992c) Can J Chem 70:2027–2032

    CAS  Article  Google Scholar 

  182. 182.

    Rettig SJ, Trotter J, Kliegel W, Becker H (1976) Can J Chem 54:3142–3151

    CAS  Article  Google Scholar 

  183. 183.

    Kliegel W, Enders B, Becker H (1982) Liebigs Ann Chem 1982:1712–1721

    Article  Google Scholar 

  184. 184.

    Kliegel W, Lubkowitz G, Rettig SJ, Trotter J (1994) Can J Chem 72:1154–1161

    CAS  Article  Google Scholar 

  185. 185.

    Kliegel W, Amt H, Becker H, Lauterbach U, Lubkowitz G, Rettig SJ, Trotter J (1994) Can J Chem 72:2118–2130

    CAS  Article  Google Scholar 

  186. 186.

    Kliegel W, Graumann J (1982) Chem-Ztg 106:378–380

    CAS  Google Scholar 

  187. 187.

    Meller A, Armbrecht M (1986) Chem Ber 119:1–8

    CAS  Article  Google Scholar 

  188. 188.

    Thiele B, Schreyer P, Englert U, Paetzold P, Boese R, Wrackmeyer B (1991) Chem Ber 124:2209–2216

    CAS  Article  Google Scholar 

  189. 189.

    Paetzold P, Richter A, Thijssen T, Wuertenberg S (1979) Chem Ber 112:3811–3827

    CAS  Article  Google Scholar 

  190. 190.

    Wang T, Wang L, Daniliuc CG, Samigullin K, Wagner M, Kehr G, Erker G (2017) Chem Sci 8:2457–2463

    CAS  PubMed  PubMed Central  Article  Google Scholar 

  191. 191.

    Ito M, Tokitoh N, Okazaki R (1998) Chem Commun 20:2495–2496

    Article  Google Scholar 

  192. 192.

    Hohaus E, Umland F (1969a) Naturwissenschaften 56:636

    CAS  Article  Google Scholar 

  193. 193.

    Jacobs RT, Lunde CS, Freund YR, Hernandez V, Li X, Xia Y, Carter DS, Berry PW, Halladay J, Rock F, Stefanakis R, Easom E, Plattner JJ, Ford L, Johnston KL, Cook DAN, Clare R, Cassidy A, Myhill L, Tyrer H, Gamble J, Guimaraes AF, Steven A, Lenz F, Ehrens A, Frohberger SJ, Koschel M, Hoerauf A, Hubner MP, McNamara CW, Bakowski MA, Turner JD, Taylor MJ, Ward SA (2019) J Med Chem 62:2521–2540

    CAS  PubMed  PubMed Central  Article  Google Scholar 

  194. 194.

    Coburn, C. A., Smith, S. W., & Dubose, R. F. (Silverback Therapeutics, Inc.); Patent WO 2019079357 Al, Apr. 25 (2019).

  195. 195.

    James, R. A., Chellappan, S. K., & Hormann, R. E. (Intrexon Corp.); Patent WO 2016/044390 Al, Mar. 24 (2016).

  196. 196.

    Behnke, M., Castro, A., Evans, C., Grenier, L., Grogan, M., Liu, T., Snyder, D., & Tibbitts, T. (Infinity Pharmaceuticals, Inc.); Patent WO 2009/126691 Al, Oct. 15 (2009).

  197. 197.

    Li, X., Lunde, C. S., Jacobs, R. T., Hernandez, V. S., Xia, Y., Plattner, J. J., Cao, K. J., Zhang, Y.-K., & Perry, M. (Anacor Pharmaceuticals, Inc., Bill and Melinda Gates Foundation.); Patent CA 2959712 A1, Sept. 2 (2017).

  198. 198.

    Dewar MJS, Dougherty RC (1964) J Am Chem Soc 86:433–436

    CAS  Article  Google Scholar 

  199. 199.

    Kliegel W, Nanninga D (1983c) J Organomet Chem 247:247–252

    CAS  Article  Google Scholar 

  200. 200.

    Sarina EA, Olmstead MM, Nguyen DN, Groziak MP (2013) Acta Cryst C 69:183–185

    CAS  Article  Google Scholar 

  201. 201.

    Davis FA, Dewar MJS, Jones R (1968) J Am Chem Soc 90:706–708

    CAS  Article  Google Scholar 

  202. 202.

    Dewar MJS, Dougherty RC (1962) J Am Chem Soc 84:2648–2649

    CAS  Article  Google Scholar 

  203. 203.

    Snyder HR, Reedy AJ, Lennarz WJ (1958) J Am Chem Soc 80:835–838

    CAS  Article  Google Scholar 

  204. 204.

    Gronowitz S, Bugge A (1965) Acta Chem Scand 19:1271–1285

    CAS  Article  Google Scholar 

  205. 205.

    Semard D, Paulmier C, Morel J, Pastour P (1972) Int J Sulfur Chem Part A 2:257–260

    CAS  Google Scholar 

  206. 206.

    Groziak MP, Chen L, Yi L, Robinson PD (1997) J Am Chem Soc 119:7817–7826

    CAS  Article  Google Scholar 

  207. 207.

    Dewar MJS, Jones R (1967) J Am Chem Soc 89:2408–2410

    CAS  Article  Google Scholar 

  208. 208.

    Dougherty RC (1968) Tetrahedron 24:6755–6772

    CAS  Article  Google Scholar 

  209. 209.

    Dunn HE, Catlin JC, Snyder HR (1968) J Org Chem 33:4483–4486

    CAS  Article  Google Scholar 

  210. 210.

    Tickell DA, Mahon MF, Bull SD, James TD (2013) Org Lett 15:860–863

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  211. 211.

    Meadows MK, Roesner EK, Lynch VM, James TD, Anslyn EV (2017) Org Lett 19:3179–3182

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  212. 212.

    Ishida N, Ikemoto W, Narumi M, Murakami M (2011) Org Lett 13:3008–3011

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  213. 213.

    Kliegel W, Lubkowitz G, Pokriefke JO, Rettig SJ, Trotter J (2000) Can J Chem 78:1325–1344

    CAS  Google Scholar 

  214. 214.

    Kliegel W, Schumacher U, Rettig SJ, Trotter J (1991) Can J Chem 69:681–686

    CAS  Article  Google Scholar 

  215. 215.

    Kliegel W, Tajerbashi M, Rettig SJ, Trotter J (1989) Can J Chem 67:1644–1649

    CAS  Article  Google Scholar 

  216. 216.

    Kliegel W, Lubkowitz G, Pokriefke JO, Rettig SJ, Trotter J (2001) Can J Chem 79:226–237

    CAS  Google Scholar 

  217. 217.

    Kliegel W, Lubkowitz G, Rettig SJ, Trotter J (1992d) Can J Chem 70:2809–2817

    CAS  Article  Google Scholar 

  218. 218.

    Kliegel W, Preu L, Schumacher U, Rettig SJ, Trotter J (1992) Can J Chem 70:1176–1187

    CAS  Article  Google Scholar 

  219. 219.

    Kliegel W (1969b) Z Chem 9:454–455

    CAS  Article  Google Scholar 

  220. 220.

    Kliegel W (1972) Justus Liebigs Ann Chem 763:61–65

    CAS  Article  Google Scholar 

  221. 221.

    Kliegel W, Ahlenstiel E (1984) J Organomet Chem 277:173–188

    CAS  Article  Google Scholar 

  222. 222.

    Kliegel W, Sarge S, Cammenga HK, Rettig SJ, Trotter J (1985) Mater Sci Monogr 28B:725–726

    CAS  Google Scholar 

  223. 223.

    Moehrle H, Fietze H (1980) Arch Pharm (Weinheim, Ger) 313:2–9

    CAS  Article  Google Scholar 

  224. 224.

    Moehrle H, Clauss E (1973) Arch Pharm (Weinheim, Ger) 306:721–729

    CAS  Article  Google Scholar 

  225. 225.

    Kliegel W, Ahlenstiel E (1977) Chem Ber 110:1623–1627

    CAS  Article  Google Scholar 

  226. 226.

    Kliegel W (1970) Z Chem 10:437–438

    CAS  Article  Google Scholar 

  227. 227.

    Kliegel W, Ahlenstiel E (1976) Chem Ber 109:3547–3556

    CAS  Article  Google Scholar 

  228. 228.

    Kliegel W, Graumann J (1984) Liebigs Ann Chem 1984:1545–1562

    Article  Google Scholar 

  229. 229.

    Kliegel W (1969c) Tetrahedron Lett 10:223–225

    Article  Google Scholar 

  230. 230.

    Kliegel W, Becker H (1977a) Chem Ber 110:2090–2097

    CAS  Article  Google Scholar 

  231. 231.

    Kliegel W, Becker H (1977b) Chem Ber 110:2067–2089

    CAS  Article  Google Scholar 

  232. 232.

    Kliegel W, Enders B, Becker H (1983) Chem Ber 116:27–45

    CAS  Article  Google Scholar 

  233. 233.

    Kliegel W, Graumann J (1983) Liebigs Ann Chem 1983:950–961

    Article  Google Scholar 

  234. 234.

    Hohaus E, Riepe W (1973) Z Naturforsch Teil B 28:440–445

    CAS  Article  Google Scholar 

  235. 235.

    Kliegel W, Preu L, Rettig SJ, Trotter J (1985) Can J Chem 63:509–515

    CAS  Article  Google Scholar 

  236. 236.

    Balaban AT, Bally I, Bishop RJ, Rentea CN, Sutton LE (1964) J Chem Soc (Resumed) 2383–2387. https://doi.org/10.1039/JR9640002383

    Article  Google Scholar 

  237. 237.

    Bode, J., Noda, H., Eros, G., & Mazunin, D. (ETH Zurich, Switz.); Patent WO 2015/104374 Al, Jul. 16 (2015).

  238. 238.

    Colclough T, Gerrard W, Lappert MF (1956) J Chem Soc (Resumed) 3006–3010. https://doi.org/10.1039/jr9560003006

    Article  Google Scholar 

  239. 239.

    Ebeling E, Kliegel W, Rettig SJ, Trotter J (1989) Can J Chem 67:933–940

    CAS  Article  Google Scholar 

  240. 240.

    Moehrle H, Gusowski B, Feil R (1971) Tetrahedron 27:221–230

    CAS  Article  Google Scholar 

  241. 241.

    Rupani P, Singh A, Rai AK, Mehrotra RC (1980) J Inorg Nucl Chem 42:1113–1116

    CAS  Article  Google Scholar 

  242. 242.

    Stempel A, Reeder E, Sternbach LH (1965) J Org Chem 30:4267–4271

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  243. 243.

    Beckert R, Hippius C, Gebauer T, Stöckner F, Lüdigk C, Weiß D, Raabe D, Günther W, Görls H (2006) Z Naturforsch B 6:437–447

    Article  Google Scholar 

  244. 244.

    Hohaus E, Umland F (1969b) Chem Ber 102:4025–4031

    CAS  Article  Google Scholar 

  245. 245.

    Maehr H, Zenchoff G, Coffen DL (1995) Biorg. Med Chem 3:391–395

    CAS  Google Scholar 

  246. 246.

    Balasubramanian V, Iyengar RR, Patel CC (1981) Indian J Chem Sect A 20A:677–679

    CAS  Google Scholar 

  247. 247.

    Kliegel W, Lubkowitz G, Rettig SJ, Trotter J (1991a) Can J Chem 69:234–238

    CAS  Article  Google Scholar 

  248. 248.

    Kliegel W, Lubkowitz G, Rettig SJ, Trotter J (1991b) Can J Chem 69:1227–1232

    CAS  Article  Google Scholar 

  249. 249.

    Golovanov IS, Sukhorukov AYu, Nelyubina YV, Khomutova YA, Ioffe SL, Tartakovsky VA (2015) J Org Chem 80:6728–6736

    CAS  PubMed  Article  PubMed Central  Google Scholar 

  250. 250.

    Semakin AN, Nelyubina YV, Ioffe SL, Sukhorukov AYu (2020) Eur J Org Chem 2020:6723–6735

    CAS  Article  Google Scholar 

  251. 251.

    Golovanov IS, Sukhorukov A Yu (2019) Izv Vyssh Uchebn Zaved Khim Khim Tekhnol 62:60–67. https://doi.org/10.6060/ivkkt.20196204.5975i

    CAS  Article  Google Scholar 

  252. 252.

    Nöth H, Regnet W (1963) Z Naturforsch B 18:1138–1139

    Article  Google Scholar 

  253. 253.

    Kuhn LP, Inatome M (1963) J Am Chem Soc 85:1206–1207

    CAS  Article  Google Scholar 

  254. 254.

    Roth HJ, Miller B (1964) Arch Pharm 297:744–747

    CAS  Article  Google Scholar 

  255. 255.

    Kliegel W, Preu L, Riebe U, Patrick BO, Rettig SJ, Trotter J (2001) Acta Cryst E 57:o943–o944

    CAS  Article  Google Scholar 

  256. 256.

    Thompson HB, Kuhn LP, Inatome M (1964) J Phys Chem 68:421–422

    CAS  Article  Google Scholar 

  257. 257.

    Kliegel W, Riebe U, Rettig SJ, Trotter J (1991) Can J Chem 69:1222–1226

    CAS  Article  Google Scholar 

  258. 258.

    Kliegel W, Drückler K, Patrick BO, Rettig SJ, Trotter J (2002) Acta Cryst E 58:o371–o373

    CAS  Article  Google Scholar 

  259. 259.

    Kliegel W, Nanninga D, Riebe U, Rettig SJ, Trotter J (1994) Can J Chem 72:1735–1740

    CAS  Article  Google Scholar 

  260. 260.

    Maringgele W, Meller A (1975) Monatsh Chem 106:1369–1374

    CAS  Article  Google Scholar 

  261. 261.

    Palmer DW, Niedenzu K (1979) Synth React Inorg Met-Org Chem 9:13–20

    CAS  Article  Google Scholar 

  262. 262.

    Jennings JR, Wade K (1967) J Chem Soc A 1333–1339. https://doi.org/10.1039/J19670001333

    Article  Google Scholar 

  263. 263.

    Meller A, Maringgele W, Koehn HG (1976) Monatsh Chem 107:89–94

    CAS  Article  Google Scholar 

  264. 264.

    Rettig SJ, Trotter J (1983) Can J Chem 61:206–210

    CAS  Article  Google Scholar 

  265. 265.

    Kliegel W, Nanninga D (1983d) Monatsh Chem 114:465–484

    CAS  Article  Google Scholar 

  266. 266.

    Hohaus E (1982) Z Anorg Allg Chem 484:41–52

    CAS  Article  Google Scholar 

  267. 267.

    Van Breemen RB, Martin LB, Schreiner AF (1988) Anal Chem 60:1314–1318

    Article  Google Scholar 

  268. 268.

    Mömming CM, Kehr G, Wibbeling B, Fröhlich R, Erker G (2010) Dalton Trans 39:7556–7564

    PubMed  Article  CAS  Google Scholar 

  269. 269.

    Zhu D, Qu Z-W, Stephan DW (2020) Dalton Trans 49:901–910

    CAS  PubMed  Article  Google Scholar 

  270. 270.

    Kliegel W, Preu L (1983) Liebigs Ann 1983:1937–1949

    Article  Google Scholar 

  271. 271.

    Kliegel W, Preu L (1984) Chem-Ztg 108:283–285

    CAS  Google Scholar 

  272. 272.

    Kliegel W, Metge J, Rettig SJ, Trotter J (1998a) Can J Chem 76:389–399

    CAS  Google Scholar 

  273. 273.

    Kliegel W, Metge J, Rettig SJ, Trotter J (1997) Can J Chem 75:1830–1843

    CAS  Article  Google Scholar 

  274. 274.

    Kliegel W, Metge J, Rettig SJ, Trotter J (1998b) Can J Chem 76:1082–1092

    CAS  Article  Google Scholar 

  275. 275.

    Kliegel W, Nanninga D (1983e) J Organomet Chem 243:373–385

    CAS  Article  Google Scholar 

  276. 276.

    Kliegel W, Motzkus H-W, Drückler K, Rettig SJ, Trotter J (1990) Can J Chem 68:64–68

    CAS  Article  Google Scholar 

  277. 277.

    Kliegel W, Tajerbashi M, Rettig SJ, Trotter J (1988) Can J Chem 66:2621–2630

    CAS  Article  Google Scholar 

  278. 278.

    Kliegel W, Barakat M, Jones PG (2004) Acta Cryst E 60:o1589–o1592

    CAS  Article  Google Scholar 

  279. 279.

    Kliegel W, Nanninga D, Rettig SJ, Trotter J (1984) Can J Chem 62:845–855

    CAS  Article  Google Scholar 

  280. 280.

    Kliegel W, Lauterbach U, Rettig SJ, Trotter J (1987) Can J Chem 65:1457–1462

    CAS  Article  Google Scholar 

  281. 281.

    Yale, H. L. (Olin Mathieson Chemical Corp.); Patent US 1961–140258, Sep. 25 (1961).

  282. 282.

    Amt H, Kliegel W, Rettig SJ, Trotter J (1990b) Can J Chem 68:1797–1802

    CAS  Article  Google Scholar 

  283. 283.

    Kliegel W, Lubkowitz G, Rettig SJ, Trotter J (1991c) Can J Chem 69:1217–1221

    CAS  Article  Google Scholar 

  284. 284.

    Kliegel W, Lubkowitz G, Rettig SJ, Trotter J (1993) Can J Chem 71:2129–2138

    CAS  Article  Google Scholar 

  285. 285.

    Rettig SJ, Trotter J, Kliegel W, Lubkowitz G (1992) Mol Cryst Liq Cryst 219:101–104

    CAS  Article  Google Scholar 

  286. 286.

    Shitov O, Ioffe S, Leont’eva L, Tartakovskii V (1973a) Zh Obshch Khim 43:1266–1271 ((CAS Accession Number: 1973:466439) (in Russian))

    CAS  Google Scholar 

  287. 287.

    Ioffe SL, Kalinin AV, Golovina TN, Khasapov BN, Tartakovskii VA (1978) Russ Chem Bull 27:816–819 ((CAS Accession Number: 1978:443544. Ioffe SL, Kalinin AV, Golovina TN, Khasapov BN, Tartakovskii VA (1978) Izv Akad Nauk SSSR Ser Khim 27:942–945 (in Russian))

    Article  Google Scholar 

  288. 288.

    Shitov OP, Ioffe SL, Leont’eva LM, Tartakovskii VA (1973b) Zh Obshch Khim 43:1127–1130 (CAS Accession Number: 1973:466429(in Russian))

    CAS  Google Scholar 

  289. 289.

    Ioffe SL, Kalinin AV, Khasapov BN, Stepanyants AU, Tartakovskii VA (1978) Russ Chem Bull 27:1009–1012 ((CAS Accession Number: 1978:507532. Ioffe SL, Kalinin AV, Khasapov BN, Stepanyants AU, Tartakovskii VA (1978) Izv Akad Nauk SSSR Ser Khim 27:1162–1165 (in Russian))

    Google Scholar 

Download references

Acknowledgements

The reported study was funded by the Russian Foundation for Basic Research (project 20-33-70188).

Author information

Affiliations

Authors

Corresponding authors

Correspondence to Ivan S. Golovanov or Alexey Yu. Sukhorukov.

Ethics declarations

Conflict of interest

The authors confirm that there are no conflicts of interest with respect to this article.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Golovanov, I.S., Sukhorukov, A.Y. Merging Boron with Nitrogen–Oxygen Bonds: A Review on BON Heterocycles. Top Curr Chem (Z) 379, 8 (2021). https://doi.org/10.1007/s41061-020-00317-3

Download citation

Keywords

  • Boron heterocycles
  • Organoboron derivatives
  • Boronic acids
  • Hydroxylamines