A facile synthesis of 2-alkyl-3-α-carboxy-α-styryl/heterylvinyl quinazolin-4(3H)-ones and 3-arylidene/heterylmethylidene-4-aroyl-1H-[1,4]benzodiazepine-2,5(3H,4H)-diones and their transformation into novel heterocyclyl and heterocyclo analogues

✍ Scribed by Poonam Gupta; Archana Sharma; R. L. Sharma

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2011
• Tongue: English
• Weight: 604 KB
• Volume: 49
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.756

✦ Synopsis

Abstract

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).