Abstract
Due to the importance of diazepines and diazepanes in medicinal chemistry and chemical biology, their preparation from diverse starting materials has been frequently reported. In this chapter, we summarize all strategies employing the method of solid-phase synthesis. More than seventeen different types of target compounds are accessible. The individual approaches are grouped according to the type of the target scaffold.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Abbreviations
- AA:
-
Amino acid
- Boc:
-
t-Butyloxycarbonyl
- BAL:
-
Backbone amide linker
- BTC:
-
Bis(trichloromethyl) carbonate
- DABCO:
-
1,4-Diazabicyclo[2.2.2]octane
- DBU:
-
1,8-Diazabicyclo[5.4.0]undec-7-ene
- DCC:
-
N,N′-Dicyclohexylcarbodiimide
- DCE:
-
Dichloroethane
- DCM:
-
Dichloromethane
- DIAD:
-
Diisopropyl azodicarboxylate
- DIBAL-H:
-
Diisobutylaluminium hydride
- DIC:
-
N,N′-Diisopropylcarbodiimide
- DIEA:
-
N,N-Diisopropylethylamine
- DEAD:
-
Diethyl azodicarboxylate
- DECP:
-
Diethyl cyanophosphonate
- DMAP:
-
4-Dimethylaminopyridine
- DMF:
-
N,N-Dimethylformamide
- DMSO:
-
Dimethyl sulfoxide
- DMTMM:
-
4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride
- EEDQ:
-
N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline
- Fmoc:
-
Fluorenylmethoxycarbonyl
- HATU:
-
[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate)
- HOBt:
-
1-Hydroxybenzotriazole
- MBHA:
-
Methylbenzhydrylamine
- NMP:
-
N-Methylpyrrolidone
- Nos:
-
Nitrobenzenesulfonyl
- TBTU:
-
N,N,N′,N′-Tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate
- TBP:
-
Tributylphosphine
- TEA:
-
Triethylamine
- THF:
-
Tetrahydrofuran
- TFA:
-
Trifluoroacetic acid
- TFMSA:
-
Trifluoromethanesulfonic acid
- TPP:
-
Triphenylphosphine
References
Charan RD, Schlingmann G, Janso J, Bernan V, Feng X, Carter GTJ (2004) Nat Prod 67(8):1431–1433
Huang RM, Ma W, Dong JD, Zhou XF, Xu T, Lee KJ, Yang X, Xu SH, Liu Y (2010) Molecules 15(2):871–877
Hadjipavlou-Litina D, Hansch C (1994) Chem Rev 94(6):1483–1505
Butcher JW, Liverton NJ, Claremon DA, Freidinger RM, Jurkiewicz NK, Lynch JJ, Salata JJ, Wang J, Dieckhaus CM, Slaughter DE, Vyas K (2003) Bioorg Med Chem Lett 13(6):1165–1168
Haynes SW, Gao X, Tang Y, Walsh CT (2012) J Am Chem Soc 134(42):17444–17447
Breslin HJ, Kukla MJ, Kromis T, Cullis H, De Knaep F, Pauwels R, Andries K, De Clercq E, Janssen MAC, Janssen PAJ (1999) Bioorg Med Chem 7(11):2427–2436
Anzini M, Canullo L, Braile C, Cappelli A, Gallelli A, Vomero S, Menziani MC, De Benedetti PG, Rizzo M, Collina S, Azzolina O, Sbacchi M, Ghelardini C, Galeotti N (2003) J Med Chem 46(18):3853–3864
Chen CY, Lee PH, Lin YY, Yu WT, Hu WP, Hsu CC, Lin YT, Chang LS, Hsiao CT, Wang JJ, Chung MI (2013) Bioorg Med Chem Lett 23(24):6854–6859
Sandra CM, Cortes Eduardo C, Simon HO, Apan Teresa R, Camacho Antonio N, Lijanova V, Marcos MG (2012) Anti-Cancer Agents Med Chem 12(6):611–618
Sternbach LH (1979) J Med Chem 22(1):1–7
Merrifield RB (1963) J Am Chem Soc 85(14):2149–2154
Kamal A, Reddy KL, Devaiah V, Shankaraiah N, Reddy DR (2006) Mini Rev Med Chem 6(1):53–69
Kaur N (2013) ChemInform 44(20)
Verma A, Ram Yadav M, Giridhar R, Prajapati N, Tripathi C, Saraf K (2013) Comb Chem High Throughput Screen 16(5):345–393
Bevacqua F, Basso A, Gitto R, Bradley M, Chimirri A (2001) Tetr Lett 42(43):7683–7685
Zhu Z, Sun ZY, Ye Y, McKittrick B, Greenlee W, Czarniecki M, Fawzi A, Zhang H, Lachowicz JE (2009) Bioorg Med Chem Lett 19(17):5218–5221
Combs AP, Saubern S, Rafalski M, Lam PY (1999) Tetr Lett 40(9):1623–1626
Ou L, Shao Z, Chen W, Giulianotti MA, Houghten RA, Yu Y (2011) Synlett 2011(15):2259–2261
Pathak R, Roy AK, Kanojiya S, Batra S (2005) Tetr Lett 46(32):5289–5292
Bunin BA, Ellman JA (1992) J Am Chem Soc 114(27):10997–10998
Bunin BA, Plunkett MJ, Ellman JA (1994) Proc Natl Acad Sci U S A 91(11):4708–4712
Plunkett MJ, Ellman JA (1995) J Am Chem Soc 117(11):3306–3307
Plunkett MJ, Ellman JA (1995) J Org Chem 60(19):6006–6007
Plunkett MJ, Ellman JA (1997) J Org Chem 62(9):2885–2893
DeWitt SH, Kiely JS, Stankovic CJ, Schroeder MC, Cody DM, Pavia MR (1993) Proc Natl Acad Sci U S A 90(15):6909–6913
Dewitt SH, Schroeder MC, Stankovic CJ, Strode JE, Czarnik AW (1994) Drug Develop Res 33(2):116–124
Lattmann E, Billington DC, Arayarat P, Singh H, Offel M (1999) Sci Asia 25(2):107–112
Laustsen LS, Sams CK (2007) J Comb Chem 9(6):1094–1103
Lattmann E, Billington DC, Poyner DR, Arayarat P, Howitt SB, Lawrence S, Offel M (2002) Drug Des Discov 18(1):9–21
Matsushita K, Okamoto C, Yoshimoto M, Harada K, Kubo M, Fukuyama Y, Hioki H (2010) J Comb Chem 12(3):311–314
Lee K, Mun SJ, Ha DC, Lee KI, Gong YD, Lee JC (2006) Bull Korean Chem Soc 27(7):974–975
Boutard N, Dufour-Gallant J, Deaudelin P, Lubell WD (2011) J Org Chem 76(11):4533–4545
Dufour-Gallant J, Chatenet D, Lubell WD (2015) J Med Chem 58(11):4624–4637
Bhalay G, Blaney P, Palmer VH, Baxter AD (1997) Tetr Lett 38(48):8375–8378
Zhang J, Goodloe WP, Lou B, Saneii H (2000) Molec Divers 5(3):127–130
Wu Z, Ercole F, FitzGerald M, Perera S, Riley P, Campbell R, Pham Y, Rea P, Sandanayake S, Mathieu MN, Bray AM, Ede NJ (2003) J Comb Chem 5(2):166–171
Hone ND, Wilson W, Reader JC (2003) Tetr Lett 44(46):8493–8495
Im I, Webb TR, Gong YD, Kim JI, Kim YC (2004) J Comb Chem 6(2):207–213
Lee JY, Im I, Webb TR, McGrath D, Song MR, Kim YC (2009) Bioorg Chem 37(3):90–95
Malik L, Kelly NM, Ma JN, Currier EA, Burstein ES, Olsson R (2009) Bioorg Med Chem Lett 19(6):1729–1732
Ali FE, Yuan CC, Ross ST, Hall LB (2000) Molec Divers 5(1):1–5
Thurston DE (1993) In: Molecular aspects of anticancer drug-DNA interactions. Springer, pp 54–88
Berry JM, Philip W, Thurston DE (2000) Tetr Lett 41(32):6171–6174
Kamal A, Reddy GSK, Raghavan S (2001) Bioorg Med Chem Lett 11(3):387–389
Kamal A, Reddy GSK, Reddy KL (2001) Tetr Lett 42(39):6969–6971
Kaplánek R, Krchňák V (2013) Tetr Lett 54(21):2600–2603
Shankaraiah N, Markandeya N, Espinoza-Moraga M, Arancibia C, Kamal A, Santos LS (2009) Synthesis 2009(13):2163–2170
Kamal A, Reddy GSK, Reddy KL, Raghavan S (2002) Tetr Lett 43(11):2103–2106
Kamal A, Reddy KL, Devaiah V, Reddy GSK (2003) Tetr Lett 44(25):4741–4745
Kamal A, Shankaraiah N, Reddy KL, Devaiah V (2006) Tetr Lett 47(25):4253–4257
Kamal A, Prabhakar S, Shankaraiah N, Markandeya N, Venkat Reddy P, Srinivasulu V, Sathish M (2013) Tetr Lett 54(33):4435–4441
Kamal A, Reddy KL, Devaiah V, Shankaraiah N, Reddy YN (2004) Tetr Lett 45(41):7667–7669
Brouillette Y, Verdié P, Martinez J, Lisowski V (2008) Synlett 2008(15):2360–2364
Ludolph B, Waldmann H (2009) Tetr Lett 50(26):3148–3150
Kamal A, Reddy KL, Devaiah V, Shankaraiah N, Suresh Kumar Reddy G, Raghavan S (2007) J Comb Chem 9(1):29–42
Kamal A, Shankaraiah N, Devaiah V, Reddy KL (2006) Tetr Lett 47(37):6553–6556
Kamal A, Shankaraiah N, Prabhakar S, Reddy C, Markandeya N, Reddy KL, Devaiah V (2008) Bioorg Med Chem Lett 18(7):2434–2439
Lee SC, Park SB (2007) Chem Commun 36:3714–3716
Lemrová B, Soural M (2012) ACS Comb Sci 14(12):645–650
Fülöpová V, Gucký T, Grepl M, Soural M (2012) ACS Comb Sci 14(12):651–656
Fülöpová V, Krchňák V (2014) ACS Comb Sci 16(8):412–420
Trapani P, Volná T, Soural M (2016) ACS Comb Sci 18(6):349–354
Fülöpová V, Funk P, Popa I, McMaster C, Soural M (2015) Eur J Org Chem 2015(16):3551–3557
Chatterjee N, Sarkar S, Pal R, Sen AK (2014) Tetr Lett 55(14):2261–2265
Nefzi A, Ong NA, Houghten RA (2001) Tetr Lett 42(31):5141–5143
Dadiboyena S, Arfaoui A, Amri H, Piedrafita FJ, Nefzi A (2015) Bioorg Med Chem Lett 25(3):685–689
Schwarz MK, Tumelty D, Gallop MA (1998) Tetr Lett 39(46):8397–8400
Lee J, Gauthier D, Rivero RA (1999) J Org Chem 64(9):3060–3065
Wu CY, Sun CM (2002) Bioorg Med Chem Lett 12(6):959–962
Herpin TF, Van Kirk KG, Salvino JM, Yu ST, Labaudiniére RF (2000) J Comb Chem 2(5):513–521
Kidwai M, Venkataramanan R (2004) Chem Heterocycl Compd 40(5):631–634
Kong KH, Chen Y, Ma X, Chui WK, Lam Y (2004) J Comb Chem 6(6):928–933
Sharma N, Chundawat TS, Mohapatra SC, Bhagat S (2013) RSC Adv 3(37):16336–16339
Goff DA, Zuckermann RN (1995) J Org Chem 60(18):5744–5745
Verdié P, Subra G, Averland-Petit MC, Amblard M, Martinez J (2008) J Comb Chem 10(6):869–874
Verdié P, Subra G, Feliu L, Sanchez P, Bergé G, Garcin G, Martinez J (2007) J Comb Chem 9(2):254–262
Mayer JP, Zhang J, Bjergarde K, Lenz DM, Gaudino JJ (1996) Tetr Lett 37(45):8081–8084
Gerdes JM, Waldmann H (2003) J Comb Chem 5(6):814–820
Migihashi C, Sato F (2003) J Heterocycl Chem 40(1):143–147
Hulme C, Ma L, Kumar NV, Krolikowski PH, Allen AC, Labaudiniere R (2000) Tetr Lett 41(10):1509–1514
Smith RA, Bobko MA, Lee W (1998) Bioorg Med Chem Lett 8(17):2369–2374
Hulme C, Peng J, Morton G, Salvino JM, Herpin T, Labaudiniere R (1998) Tetr Lett 39(40):7227–7230
Chen JJ, Golebiowski A, Klopfenstein SR, West L (2002) Tetr Lett 43(22):4083–4085
Kennedy AL, Fryer AM, Josey JA (2002) Org Lett 4(7):1167–1170
Jeon MK, Kwon JJ, Kim MS, Gong YD (2008) Synlett 2008(11):1651–1656
Boojamra CG, Burow KM, Ellman JA (1995) J Org Chem 60(18):5742–5743
Ettmayer P, Chloupek S, Weigand K (2003) J Comb Chem 5(3):253–259
Joseph CG, Wilson KR, Wood MS, Sorenson NB, Phan DV, Xiang Z, Witek RM, Haskell-Luevano C (2008) J Med Chem 51(5):1423–1431
Rivero IA, Peralta M, Heredia S, Madrigal D, Pina-Luis G, Chávez D (2003) Arkivoc 2003(11):27–36
Nefzi A, Ostresh JM, Houghten RA (1997) Tetr Lett 38(28):4943–4946
Nefzi A, Dooley C, Ostresh JM, Houghten RA (1998) Bioorg Med Chem Lett 8(17):2273–2278
Moure A, Sanclimens G, Bujons J, Masip I, Alvarez-Larena A, Pérez-Payá E, Alfonso I, Messeguer A (2011) Chem Eur J 17(28):7927–7939
Krchňák V, Weichsel AS (1997) Tetr Lett 38(42):7299–7302
Giovannoni J, Subra G, Amblard M, Martinez J (2001) Tetr Lett 42(32):5389–5392
Caroen J, Clemmen A, Kámán J, Backaert F, Goeman JL, Fülöp F, Van der Eycken J (2016) Tetrahedron 72(1):148–160
Sülli-Vargha H, Schlosser G, Ilaš J (2007) J Peptide Sci 13(11):742–748
Lampariello LR, Piras D, Rodriquez M, Taddei M (2003) J Org Chem 68(20):7893–7895
Xu JF, Huang X (2009) J Comb Chem 11(5):938–942
Cao J, Huang X (2010) J Comb Chem 12(1):1–4
Huang X, Cao J, Huang J (2009) J Comb Chem 11(4):515–518
Olsen CA, Christensen C, Nielsen B, Farah MM, Witt M, Clausen RP, Kristensen JL, Franzyk H, Jaroszewski JW (2006) Org Lett 8(15):3371–3374
Ottesen LK, Olsen CA, Witt M, Jaroszewski JW, Franzyk H (2009) Chem Eur J 15(12):2966–2978
Li D, Hall DG (2005) Tetrahedron: Asymmetry 16(10):1733–1736
Eans SO, Ganno ML, Mizrachi E, Houghten RA, Dooley CT, McLaughlin JP, Nefzi A (2015) J Med Chem 58(12):4905–4917
Vaňková B, Brulíková L, Wu B, Krchňák V (2012) Eur J Org Chem 2012(26):5075–5084
Ventosa-Andrés P, Barea Ripoll CA, La-Venia A, Krchňák V (2015) Tetr Lett 56(40):5424–5428
Acknowledgments
The authors are grateful to project CZ.1.07/2.3.00/20.0009 from the European Social Fund and the National Program of Sustainability (project LO1304).
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2017 Springer International Publishing AG
About this chapter
Cite this chapter
Fülöpová, V., Soural, M. (2017). Solid-Phase Synthesis of Seven-Membered Heterocycles with Two Nitrogen Atoms. In: Krchňák , V. (eds) Solid-Phase Synthesis of Nitrogenous Heterocycles. Topics in Heterocyclic Chemistry, vol 52. Springer, Cham. https://doi.org/10.1007/7081_2016_2
Download citation
DOI: https://doi.org/10.1007/7081_2016_2
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-58615-1
Online ISBN: 978-3-319-58616-8
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)