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Diversity Oriented Synthesis of Indoloazepinobenzimidazole and Benzimidazotriazolobenzodiazepine from N 1 ‐Alkyne‐1,2‐diamines
Author(s) -
Kumar Ravi,
Arigela Rajesh K.,
Samala Srinivas,
Kundu Bijoy
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502956
Subject(s) - alkyne , aromatization , chemistry , benzimidazole , ring (chemistry) , block (permutation group theory) , stereochemistry , medicinal chemistry , mathematics , organic chemistry , catalysis , combinatorics
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.