Some Reactions of 6,8-Dibromo-2-Propenyl-4h-3,1-Benzoxazin-4-One With Nitrogen Nucleophiles Under Microwave Irradiation

Abstract

The benzoxazinone derivative (1) was prepared upon the action of crotonoyl chloride on 3,5-dibromoanthranilic acid in pyridine. Microwave irradiation assisted the aminolysis of (1) with nitrogen nucleophiles as benzyl amine, hydrazine hydrate and formamide to give the amide derivatives (2a-c) respectively. Quinazolinone derivatives (3a-e) were produced upon the action of primary amines such as m-nitroaniline, p-toluidine, p-anisidine, benzyl amine and/or hydrazine hydrate respectively on the benzoxazinone derivative (1). An excess amount of p-anisidine, phenylhydrazine and/or p-toluidine afforded the amide and quinazolinone derivatives (4a & 5a), (4b & 5b) and/or (5c) respectively. The benzoxazinone derivative (1) was subjected to react with secondary amines as piperidine or morpholine giving the amide derivatives (6a) or (6b) respectively under 1 : 1 molar ratio, while under 1 : 2 molar ratio, the dipiperidiyl or dimorphonyl derivatives (7a) or (7b) were formed respectively. Ammonolysis of (1) using ammonium acetate, yielded the quinazolinone derivative (8).