Log in

Syntheses of novel diaryl[d,f ][1,3]diazepines via one-pot Suzuki coupling followed by direct ring closure with carboxylic acids

  • Full-Length Paper
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

A series of novel and diverse diaryl[d,f][1,3]diazepines were designed and synthesized to expand the pharmaceutical utility of the [6,7]bicyclic molecular skeletons. The facile synthesis involved two key steps: a one-pot Suzuki coupling to construct the bi-aryl intermediates from corresponding halides, and a ring closure by direct condensation with carboxylic acids.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Antonow D, Thurston DE (2011) Synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines (PBDs). Chem Rev 111: 2815–2864. doi:10.1021/cr100120f

    Article  PubMed  CAS  Google Scholar 

  2. PDR Staff (2011) Physicians’ desk reference, 65th edn. PDR Network, Montvale

  3. Cipolla L, Araujo AC, Airoldi C, Bini D (2009) Pyrrolo[2,1-c][1,4]benzodiazepine as a scaffold for the design and synthesis of anti-tumour drugs. Anti-Cancer Agents Med Chem 9: 1–31. doi:10.2174/187152009787047743

    CAS  Google Scholar 

  4. Geyer HM, Martin LL, Crichlow CA, Dekow FW, Ellis DB, Kruse H, Setescak LL, Worms M (1982) (±)-4-Ary1-4,5-dihydro-3H-l,3-benzodiazepines. 1. Synthesis and evaluation of (±)-4,5-dihydro-2,3-dimethyl-4-phenyl-3H-1,3-benzodiazepine and analogues as potential antidepressant agents. J Med Chem 25: 340–346. doi:10.1021/jm00346a003

    Article  PubMed  CAS  Google Scholar 

  5. Nichols PL, Skidmore J, Ward RW, Wilson DM (2008) 5-Phenyl-1,3,4-oxadiazol-2-yl-acetyl-4-piperidinyl derivatives as CGRP receptor antagonists. Patent WO2009000819

  6. Zhu Z, Sun ZY, Ye Y, McKittrick B, Greenlee W, Czarniecki M, Fawzi A, Zhang H, Lachowicz JE (2009) Design and discovery of 1,3-benzodiazepines as novel dopamine antagonists. Bioorg Med Chem Lett 19: 5218–5221. doi:10.1016/j.bmcl.2009.07.012

    Article  PubMed  CAS  Google Scholar 

  7. Takayama T, Umemiya H, Amada H, Yabuuchi T, Koami T, Shiozawa F, Oka Y, Takaoka A, Yamaguchi A, Endo M, Sato M (2010) Ring-fused pyrazole derivatives as potent inhibitors of lymphocyte-specific kinase (Lck): structure, synthesis, and SAR. Bioorg Med Chem Lett 20: 112–116. doi:10.1016/j.bmcl.2009.11.013

    Article  PubMed  CAS  Google Scholar 

  8. Rotas G, Natchkebia K, Natsvlishvil N, Kekelidze M, Kimbaris A, Varvounis G, Mikeladze D (2005) Action of a novel pyrrolo[1,2-c][1.3]benzodiazepine on the viability of Jurkat and neuronal/glial cells. Bioorg Med Chem Lett 20: 3220–3223. doi:10.1016/j.bmcl.2005.05.006

    Article  Google Scholar 

  9. Rotas G, Kimbaris A, Varvounis G (2011) Synthesis of a novel pyrrolo[1,2-c][1.3] benzodiazepine analogue of VPA-985. Tetrahedron 67: 7805–7810. doi:10.1016/j.tet.2011.07.083

    Article  CAS  Google Scholar 

  10. Fukamachi S, Kobayashi A, Konishi H, Kobayashi K (2010) A convenient synthesis of new types of benzodiazepine derivatives: 2-alkylsulfanyl-3H-4,5-dihydro-1,3-benzodiazepin-4-ones and 2-alkylsulfanyl-3H-4,5-dihydro-1,3-benzodiazepine-4-thiones. Synthesis 288–292. doi:10.1055/s-0029-1217100

  11. Dengiz C, Ozcan S, Sahin E, Balci M (2010) New synthetic methodology for construction of the 1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-one skeleton. Synthesis 1365–1370. doi:10.1055/s-0029-1218673

  12. Ried W, Sinharay A (1964) Note for the ring closure reaction of o,o-diamino-biphenyl. Chem Ber 97: 1214–1215

    Article  CAS  Google Scholar 

  13. Ried W, Sinharay A (1965) More for the ring closure reaction of o,o-diamino-biphenyl. Chem Ber 98: 3523–3531

    Article  CAS  Google Scholar 

  14. Kaczmarek L, Nantka-Namirski P (1990) Synthesis of N-monosubstituted-3,3′diamines. Monatsh Chem 121: 821–828. doi:10.1007/BF00808375

    Article  CAS  Google Scholar 

  15. Matsuda K, Yanagisawa I, Isomura Y, Mase T, Shibanuma T (1997) Alternative synthesis of dibenzo- and dipyrido-[1,3]diazepines from thioamides and o,o′-diaminobiaryls. Synth Commun 27: 2393–2402. doi:10.1080/00397919708004101

    Article  CAS  Google Scholar 

  16. Trzewik B, Ciez D, Hodorowicz M, Stadnicka K (2008) Newα-amido-α-aminonitrones as building blocks for constructing heterocyclic systems. Synthesis 18: 2977–2985. doi:10.1055/s-2008-1067236

    Article  Google Scholar 

  17. Zaleska B, Karelus M, Trzewik B, Serda P (2007) A new way to quinazolines, perimidines and dibenzo[d,f][1,3]diazepines. J Chem Res 4: 195–199. doi:10.3184/030823407X203387

    Article  Google Scholar 

  18. Maddaford SP, Keay BA (1994) Scope and limitations of the palladium-catalyzed cross-coupling reaction of in situ generated organoboranes with aryl and vinyl halides. J Org Chem 59: 6501–6503. doi:10.1021/jo00101a001

    Article  CAS  Google Scholar 

  19. Baudoin O, Guenard D, Gueritte F (2000) Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2′-disubstituted biphenyls. J Org Chem 65: 9268–9271. doi:10.1021/jo005663d

    Article  PubMed  CAS  Google Scholar 

  20. Broutin PE, Cerna I, Campaniello M, Leroux F, Colobert F (2004) Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki–Miyaura biphenyl synthesis. Org Lett 6: 4419–4422. doi:10.1021/ol048303b

    Article  PubMed  CAS  Google Scholar 

  21. Brown SD, Armstrong RW (1996) Synthesis of tetrasubstituted ethylenes on solid support via resin capture. J Am Chem Soc 118: 6331–6332. doi:10.1021/ja961203j

    Article  CAS  Google Scholar 

  22. Akkaoui AE, Berteina-Raboin S, Mouaddib A, Guillaumet G (2010) Direct arylation of imidazo[1,2-b]pyridazines: microwave-assisted one-pot Suzuki coupling/Pd-catalysed arylation. Eur J Org Chem 862–871 doi:10.1002/ejoc.200900849

  23. Lam KC, Marder TB, Lin Z (2010) Mechanism of the palladium-catalyzed borylation of aryl halides with pinacolborane. Organometallics 29: 1849–1857. doi:10.1021/om9010802

    Article  CAS  Google Scholar 

  24. Yamamoto T, Morita T, Takagi J, Yamakawa T (2011) NiCl2(PMe3)2-catalyzed borylation of aryl chlorides. Org Lett 13: 5766–5769. doi:10.1021/ol202267t

    Article  PubMed  CAS  Google Scholar 

  25. Slevin A, Koolmeister T, Scobie M (2007) A versatile synthesis of diverse 3,4-fused cinnolines via the base catalysed condensation of 2-amino-2′-nitrobiaryls. Chem Commun 24: 2506–2508. doi:10.1039/B618318B

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yazhong Pei.

Electronic Supplementary Material

The Below is the Electronic Supplementary Material.

ESM 1 (DOC 6,937 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yan, L., Che, X., Bai, X. et al. Syntheses of novel diaryl[d,f ][1,3]diazepines via one-pot Suzuki coupling followed by direct ring closure with carboxylic acids. Mol Divers 16, 489–501 (2012). https://doi.org/10.1007/s11030-012-9382-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-012-9382-1

Keywords

Navigation