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Benzotriazole-Mediated Synthesis of Oxygen-Containing Heterocycles

  • Oleg I. BolshakovEmail author
Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 43)

Abstract

This review aims at delivering an overview of the synthetic utility of benzotriazole and its derivatives for the preparation of oxygen-containing heterocycles. This review serves both as a synthetic guide and as a theoretical handbook of benzotriazole-assisted preparations of oxygen heterocycles and offers a complete overview of existing applications for benzotriazole and its derivatives in heterocyclic synthesis. Multiple examples reveal the superiority of benzotriazole-based approaches over conventional ones.

Keywords

1H-1,2,3-Benzotriazole Carbanions Cyclization Cycloaddition Furans Oxadiazoles Oxazepines Oxazines Oxazoles Oxazolidines Oxiranes Pyrans β-Lactones 

Abbreviations

(P(C6H5)3)2PdCl2

Bis(triphenylphosphine)palladium(II) dichloride

BtH

1H-1,2,3-Benzotriazole

BuLi

Butyllithium

CH3CN

Acetonitrile

DBU

1,8-Diazabicyclo[5.4.0]undec-7-ene

DCM

Dichloromethane

DMD

3,3-Dimethyldioxirane

DME

Dimethoxyethane

DMF

Dimethylformamide

DMSO

Dimethylsulfoxide

E

Electrophile

h

Hour

Hal

Halogen

HMPA

Hexamethylphosphoramide

i-PrOH

2-Propanol

LDA

Lithium diisopropylamide

LiHMDS

Lithium hexamethyldisilazide

m-CPBA

3-Chloroperbenzoic acid

NIS

N-Iodosuccinimide

NMP

N-Methyl-2-pyrrolidone

Py

Pyridine

rt

Room temperature

t-BuOH

tert-Butyl alcohol

t-BuOK

Potassium tert-butoxide

TFA

Trifluoroacetic acid

THF

Tetrahydrofuran

TMSCl

Trimethylchlorosilane

TsOH

4-Toluene sulfonic acid

References

  1. 1.
    Katritzky AR, Rees CW (eds) (1984) Comprehensive Heterocyclic Chemistry, vols 1–8. Pergamon, OxfordGoogle Scholar
  2. 2.
    Katritzky AR, Rees CW, Scriven EFV (eds) (1996) Comprehensive heterocyclic chemistry II, vols 1–11. Pergamon, OxfordGoogle Scholar
  3. 3.
    Katritzky AR, Ramsden CA, Scriven EFV, Taylor RJK (eds) (2008) Comprehensive heterocyclic chemistry III (2008) vols 1–15. Elsevier, OxfordGoogle Scholar
  4. 4.
    Katritzky AR, Wu H, Xie L, Rachwal S, Rachwal B, Jiang J, Zhang G, Lang H (1995) Synthesis 10:1315–1323CrossRefGoogle Scholar
  5. 5.
    Katritzky AR, Rachwal S (2010) Chem Rev 110(3):1564–1610CrossRefGoogle Scholar
  6. 6.
    Katritzky AR, Rachwal S (2011) Chem Rev 111(11):7063–7120CrossRefGoogle Scholar
  7. 7.
    Katritzky AR, Lan X, Fan WQ (1994) Synthesis 1(5):445–456CrossRefGoogle Scholar
  8. 8.
    Katritzky AR, Qi M (1998) Tetrahedron 54(12):2647–2668CrossRefGoogle Scholar
  9. 9.
    Katritzky AR, Qi M (1998) Coll Czechoslovak Chem Comm 63(5):599–613CrossRefGoogle Scholar
  10. 10.
    Katritzky AR, Toader D (2001) Synlett 4:458–466Google Scholar
  11. 11.
    Katritzky AR, Rogovoy BV (2003) Chem Europ J 9(19):4586–4593CrossRefGoogle Scholar
  12. 12.
    Katritzky AR, Manju K, Singh SK, Meher NK (2005) Tetrahedron 61(10):2555–2581CrossRefGoogle Scholar
  13. 13.
    Katritzky AR, Kirichenko K (2006) Arkivoc 4:119–151Google Scholar
  14. 14.
    Katritzky AR, Angrish P, Todadze E (2009) Synlett 15:2392–2411CrossRefGoogle Scholar
  15. 15.
    Avan I, Dennis HC, Katritzky AR (2014) Chem Soc Rev 43(10):3575–3594CrossRefGoogle Scholar
  16. 16.
    Katritzky AR, Jiang J (1995) J Org Chem 60:7597–7604CrossRefGoogle Scholar
  17. 17.
    Katritzky AR, Xie L, Serdyuk L (1996) J Org Chem 61:7564–7570CrossRefGoogle Scholar
  18. 18.
    Katritzky AR, Manju K, Steel PJ (2003) J Org Chem 68:407–411CrossRefGoogle Scholar
  19. 19.
    Katritzky AR, Manju K, Gromova AV, Steel PJ (2004) J Org Chem 69:6018–6023CrossRefGoogle Scholar
  20. 20.
    Degennaro L, Capriati V, Carlucci C, Florio S, Luisi R, Nuzzo I, Cuocci C (2009) Tetrahedron 65:8745–8755Google Scholar
  21. 21.
    Xiao X, Lin D, Tong S, Mo H (2011) Synlett 19:2823–2826CrossRefGoogle Scholar
  22. 22.
    Katritzky AR, Heck KA, Li J, Wells A, Garot C (1996) Synt Commun 26(14):2657–2670CrossRefGoogle Scholar
  23. 23.
    Katritzky AR, Maimait R, Denisenko A, Denisenko SN (2001) Arkivoc 5:68–78Google Scholar
  24. 24.
    Wedler C, Kleiner K, Kunath A, Schick H (1996) Liebigs Ann 5:881–885Google Scholar
  25. 25.
    Danheiser RL, Nowick JS (1991) J Org Chem 56:1176–1185CrossRefGoogle Scholar
  26. 26.
    Wedler C, Kunath A, Schick H (1995) J Org Chem 60:758–760CrossRefGoogle Scholar
  27. 27.
    Zhi J, Melia AT, Guerciolini R, Ching J, Kinberg J, Hauptman JB, Patel IH (1994) Clin Pharm Ther 56:82–85CrossRefGoogle Scholar
  28. 28.
    Wedler C, Costisella B, Schick H (1999) J Org Chem 64:5301–5303CrossRefGoogle Scholar
  29. 29.
    Pleynet DPM, Dutton JK, Thornton-Pett M, Johnson AP (1995) Tetrahedron Let 36(35):6321–6324CrossRefGoogle Scholar
  30. 30.
    Dutton JK, Pleynet DPM, Johnson P (1999) Tetrahedron 55:11927–11942CrossRefGoogle Scholar
  31. 31.
    Katritzky AR, Lan X, Zhang Z (1993) J Heterocycl Chem 30(2):381–387CrossRefGoogle Scholar
  32. 32.
    Katritzky AR, Li J, Gordeev MF (1993) J Org Chem 58:3038–3041CrossRefGoogle Scholar
  33. 33.
    Katritzky AR, Li J (1995) J Org Chem 60:638–643CrossRefGoogle Scholar
  34. 34.
    Katritzky AR, Fali CN, Li J (1997) J Org Chem 62:8205–8209CrossRefGoogle Scholar
  35. 35.
    Katritzky AR, Verin SV (1995) J Heterocycl Chem 32:323–328CrossRefGoogle Scholar
  36. 36.
    Katritzky AR, Yang B, Jiang J, Steel PJ (1995) Heterocycles 41:765–772CrossRefGoogle Scholar
  37. 37.
    Katritzky AR, Cheng D, Leeming P, Ghiviriga I (1996) J Heterocycl Chem 33(6):1935–1941CrossRefGoogle Scholar
  38. 38.
    Katritzky AR, Serdyuk L, Xie L (1998) J Chem Soc Perkin Trans 1 6:1059–1064Google Scholar
  39. 39.
    Katritzky AR, Ji Y, Fang Y, Prakash I (2001) J Org Chem 66:5613–5615CrossRefGoogle Scholar
  40. 40.
    Katritzky AR, Kirichenko K, Hür D, Zhao X, Ji Y, Steel PJ (2004) Arkivoc 6:27–44Google Scholar
  41. 41.
    Katritzky AR, Jiang J (1995) J Org Chem 60:6–7CrossRefGoogle Scholar
  42. 42.
    Katritzky AR, Lan X (1992) Synthesis 8:761–764CrossRefGoogle Scholar
  43. 43.
    Katritzky AR, Lan X, Yang JZ, Denisko OV (1998) Chem Rev 98:409–548CrossRefGoogle Scholar
  44. 44.
    Katritzky AR, Wang X, Xie L, Toader D (1998) J Org Chem 63:3445–3449CrossRefGoogle Scholar
  45. 45.
    Moody CJ, Whitham GH (1992) Reactive intermediates. Oxford University Press, New YorkGoogle Scholar
  46. 46.
    Birkett MA, Knight DW, Little PB, Mitchell MB (2000) Tetrahedron 56:1013–1023CrossRefGoogle Scholar
  47. 47.
    Knight DW, Little PB (2000) J Chem Soc Perkin Trans 1 15:2343–2355Google Scholar
  48. 48.
    Knight DW, Little PB (1998) Tetrahedron Let 39(28):5105–5108CrossRefGoogle Scholar
  49. 49.
    Knight DW, Qing X (2009) Tetrahedron Let 50(26):3534–3537CrossRefGoogle Scholar
  50. 50.
    Knight DW, Little PB (1998) Synlett 10:1141–1143CrossRefGoogle Scholar
  51. 51.
    Knight DW, Little PB (2001) J Chem Soc Perkin Trans 1 15:1771–1777Google Scholar
  52. 52.
    Katritzky AR, Denisko OV (2002) J Org Chem 67:3104–3108CrossRefGoogle Scholar
  53. 53.
    Yu T, Zhao Y, Fan D (2006) J Molec Struc 791:18–22CrossRefGoogle Scholar
  54. 54.
    Yu T, Zhang P, Zhao Y, Zhang H, Fan D, Dong W, Ding L (2009) Phosp Sulf Silic 184(10):2655–2663CrossRefGoogle Scholar
  55. 55.
    Katritzky AR, Qi M, Feng D, Nichols DA (1997) J Org Chem 62:4121–4124CrossRefGoogle Scholar
  56. 56.
    Katritzky AR, Feng D, Qi M (1997) J Org Chem 62:6222–6225CrossRefGoogle Scholar
  57. 57.
    Katritzky AR, Rachwal S, Rachwal BJ (1987) J Soc Perkin Trans 1:799–804CrossRefGoogle Scholar
  58. 58.
    Katritzky AR, Feng D, Qi M (1998) Tetrahedron Let 39:6835–6836CrossRefGoogle Scholar
  59. 59.
    Katritzky AR, Cai C, Suzuki K, Singh SK (2004) J Org Chem 69:811–814CrossRefGoogle Scholar
  60. 60.
    Katritzky AR, Drewniak M (1988) J Chem See Perkin Trans 1:2339–2344CrossRefGoogle Scholar
  61. 61.
    Katritzky AR, Chen YX, Yannakopoulou K, Lue P (1989) Tetrahedron Let 30(48):6657–6660CrossRefGoogle Scholar
  62. 62.
    Katritzky AR, Wu H, Xie L (1995) J Heterocycl Chem 32:1651–1652CrossRefGoogle Scholar
  63. 63.
    Katritzky AR, Qiu G, Yang B, Steel PG (1998) J Org Chem 63:6699–6703CrossRefGoogle Scholar
  64. 64.
    Katritzky AR, Cui XL, Yang B, Steel PG (1998) Tetrahedron Let 39:1697–1700CrossRefGoogle Scholar
  65. 65.
    Katritzky AR, Singh SK, Bobrov S (2004) J Org Chem 69:9313–9315CrossRefGoogle Scholar
  66. 66.
    Al-Awadi NA, George BJ, Dib HH, Ibrahim MR, Ibrahim YA (2005) Tetrahedron 61:8257–8263CrossRefGoogle Scholar
  67. 67.
    Katritzky AR, Hitchings GJ, Zhao X (1990) J Chem Soc Perkin Trans 1:2371–2377CrossRefGoogle Scholar
  68. 68.
    Katritzky AR, Wang M, Zhang S, Voronkov MV (2001) J Org Chem 66:6787–6791CrossRefGoogle Scholar
  69. 69.
    Kuehne ME, Weaver SJ, Franz P (1964) J Org Chem 29:1582–1586CrossRefGoogle Scholar
  70. 70.
    Katritzky AR, Musgrave RP, Breytenbach JC (1996) J Heterocycl Chem 33:1637–1646CrossRefGoogle Scholar
  71. 71.
    Katritzky AR, Button MAC, Denisenko SN (2000) J Heterocycl Chem 37:1505–1510CrossRefGoogle Scholar
  72. 72.
    Katritzky AR, Shestopalov AA, Suzuki K (2005) Arkivoc 7:36–55Google Scholar
  73. 73.
    Katritzky AR, Huang TB, Voronkov MV (2000) J Org Chem 65:2246–2248CrossRefGoogle Scholar
  74. 74.
    Katritzky AR, Vvedensky V, Cai X, Rogovoy B, Steel PJ (2002) Arkivoc 6:82–90Google Scholar
  75. 75.
    Katritzky AR, Gupta V, Gordeev M (1993) J Heterocycl Chem 30(4):1073–1077CrossRefGoogle Scholar
  76. 76.
    Katritzky AR, Offerman RJ, Cabildo P, Soleimen M (1988) Recl Trav Chim PayBass 107:641–645CrossRefGoogle Scholar
  77. 77.
    Katritzky AR, Pernak J (1992) Fan WQ. J pract Chem 334:114–118CrossRefGoogle Scholar
  78. 78.
    Katritzky AR, Zhang G, Jiang J (1995) J Org Chem 60:7625–7630CrossRefGoogle Scholar
  79. 79.
    Katritzky AR, Singh SK, Akhmedova R, Cai C, Bodroy S (2007) Arkivoc 6:6–13Google Scholar
  80. 80.
    Katritzky AR, Xu YJ, He HY, Mehta S (2001) J Org Chem 66:5590–5594CrossRefGoogle Scholar

Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  1. 1.South Ural State UniversityChelyabinskRussia

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