Display options
Cite
Kumar R, Arigela RK, Samala S, et al. Diversity Oriented Synthesis of Indoloazepinobenzimidazole and Benzimidazotriazolobenzodiazepine from N(1)-Alkyne-1,2-diamines. Chemistry. 2015;21(51):18828-33doi: 10.1002/chem.201502956.
Kumar, R., Arigela, R. K., Samala, S., & Kundu, B. (2015). Diversity Oriented Synthesis of Indoloazepinobenzimidazole and Benzimidazotriazolobenzodiazepine from N(1)-Alkyne-1,2-diamines. Chemistry (Weinheim an der Bergstrasse, Germany), 21(51), 18828-33. https://doi.org/10.1002/chem.201502956
Kumar, Ravi, et al. "Diversity Oriented Synthesis of Indoloazepinobenzimidazole and Benzimidazotriazolobenzodiazepine from N(1)-Alkyne-1,2-diamines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,51 (2015): 18828-33. doi: https://doi.org/10.1002/chem.201502956
Kumar R, Arigela RK, Samala S, Kundu B. Diversity Oriented Synthesis of Indoloazepinobenzimidazole and Benzimidazotriazolobenzodiazepine from N(1)-Alkyne-1,2-diamines. Chemistry. 2015 Dec 14;21(51):18828-33. doi: 10.1002/chem.201502956. Epub 2015 Nov 03. PMID: 26525303.
Copy Download .nbib Format: NLM
Share it on

Chemistry. 2015 Dec 14;21(51):18828-33. doi: 10.1002/chem.201502956. Epub 2015 Nov 03.

Diversity Oriented Synthesis of Indoloazepinobenzimidazole and Benzimidazotriazolobenzodiazepine from N(1)-Alkyne-1,2-diamines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Ravi Kumar, Rajesh K Arigela, Srinivas Samala, Bijoy Kundu

Affiliations

  1. Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, 226031 (India).
  2. Academy of Scientific and Innovative Research, New Delhi, 110001 (India).
  3. Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, 226031 (India). [email protected].
  4. Academy of Scientific and Innovative Research, New Delhi, 110001 (India). [email protected].

PMID: 26525303 DOI: 10.1002/chem.201502956

Abstract

A one-pot protocol for the diversity oriented synthesis of two N-polyheterocycles indoloazepinobenzimidazole and benzimidazotriazolobenzodiazepine from a common N(1)-alkyne-1,2-diamine building block is described. The approach involves sequential formation of benzimidazole through cyclocondensation and oxidation, which is followed by the formation of either an azepine ring (through alkyne activation and 6-endo-dig cyclization, 1,2-migration with ring expansion, and re-aromatization), or diazepine and triazole rings through 1,3-dipolar cycloaddition.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: CC activation; cycloaddition; fused-ring systems; heterocycles; rearrangement

Publication Types