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Expeditious Synthesis of Imidazole‐ and Pyrrole‐Fused Benzodiazocines
Author(s) -
Mishra Amita,
Batra Sanjay
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000355
Subject(s) - chemistry , imidazole , pyrrole , saponification , acrylate , amide , intramolecular force , ethyl acrylate , organic chemistry , medicinal chemistry , stereochemistry , combinatorial chemistry , monomer , polymer
A straightforward strategy for the synthesis of imidazole‐fused benzodiazocine from 1‐(2‐nitrophenyl)‐1 H ‐imidazole‐2‐carbaldehyde via Morita–Baylis–Hillman reaction followed by reductive intramolecular cyclization is described. Alternatively the Horner–Wadsworth–Emmons reaction of this substrate with triethyl phosphonoacetate yielded ( E )‐ethyl 3‐(1‐(2‐nitrophenyl)‐1 H ‐imidazol‐2‐yl)acrylate which upon sequential reduction, saponification and amide coupling furnished imidazole‐fused diazocinones. On the other hand, 1‐(2‐nitrophenyl)‐1 H ‐pyrrole‐2‐carbaldehyde failed to undergo the Morita–Baylis–Hillman reaction but successfully yields ( E )‐ethyl 3‐(1‐(2‐nitrophenyl)‐1 H ‐pyrrol‐2‐yl)acrylate via Horner–Wadsworth–Emmons reaction which through a similar series of reaction as for imidazole produced pyrrole‐fused diazocinone in good yields.