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A facile synthesis of 2‐alkyl‐3‐α‐carboxy‐α‐styryl/heterylvinyl quinazolin‐4(3 H )‐ones and 3‐arylidene/heterylmethylidene‐4‐aroyl‐1 H ‐[1,4]benzodiazepine‐2,5(3 H ,4 H )‐diones and their transformation into novel heterocyclyl and heterocyclo analogues
Author(s) -
Gupta Poonam,
Sharma Archana,
Sharma R. L.
Publication year - 2012
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.756
Subject(s) - chemistry , benzodiazepine , quinazoline , medicinal chemistry , acetic acid , alkyl , condensation , stereochemistry , organic chemistry , receptor , biochemistry , physics , thermodynamics
Condensation of 2‐methyl‐/2‐ethyl‐ and 2‐phenyl‐/p‐tolyl‐4‐arylidene‐/heterylmethylidene‐2‐oxazolin‐5‐ones (γ‐azlactones) 2 with o‐aminobenzamide 1 in acetic acid resulted in the formation of two entirely different heterocyclic systems, differently substituted quinazoline compounds, 2‐methyl‐/2‐ethyl‐3‐α‐carboxy‐α‐styryl‐/β‐heteryl‐α‐carboxyvinyl‐quinazolin‐4(3 H )‐ones 3a–3e and 3′a–3′e and differently substituted 1,4‐benzodiazepine compounds, 3‐arylidene‐/heteryl methylidene‐4‐aroyl‐1 H ‐[1,4]benzodiazepine‐2,5(3 H ,4 H )‐diones 7a–7e and 7′a–7′e . Compounds 3a–3e and 3′a–3′e have been converted into compounds, 4a–4e and 4′a–4′e; 5a–5e, and 5′a–5′e; and 6a–6e and 6′a–6′e through different transformations. Benzodiazepines, 7a–7e and 7′a–7′e , on condensation with o ‐phenylenediamine have generated three novel heterocyclic systems 8a–8e and 8′a–8′e; 9a–9e and 9′a–9′e; and 10a–10e and 10′a–10′e . J. Heterocyclic Chem., (2012).