Synthesis and behaviour of 2-carboxyvinyl-6,8-dibromo-4H-3,1-benzoxazin-4-one towards nitrogen,carbon and sulphur nucleophiles

摘要

6,8-dibromo-4H-3,1-benzoxazinone 2 is synthesized and allowed to react with some nitrogen nucleophiles namely,p-toluidine,hydroxylamine hydrochloride,ethanolamine,and glycine and affords 3-substituted quinazolinones 3-6,while with isobutylamine and benzylamine results benzamide derivatives 7,8.Compound 4 is subjected to acylation and alkylation and produces 9-11 respectively.Alkylation of compound 5 with 2-naphthol and benzamide yields 12,13.Treatment of benzoxazinone 2 with o-phenylenediamine in different solvents under different conditions affords the substituted benzamide 14 and 3-substitutedquinazolinone 15.