SOME REACTIONS OF 6,8-DIBROMO-2-PROPENYL-4H-3,1-BENZOXAZIN-4-ONE WITH NITROGEN NUCLEOPHILES UNDER MICROWAVE IRRADIATION | ||||
| Al-Azhar Bulletin of Science | ||||
| Article 3, Volume 2007, Issue 6, June 2007, Page 163-171 PDF (228.96 K) | ||||
| Document Type: Original Article | ||||
| DOI: 10.21608/absb.2007.10873 | ||||
 View on SCiNiTO | ||||
| Authors | ||||
| A. A. ABDALHA* ; M. K. ABOU EL-REGAL; M. A. EL-KASSABY; A. M. NAZEER | ||||
| Chemistry Department, Faculty of Science, Ain Shams University, Abbassia, Cairo, Egypt | ||||
| 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). | ||||
| Keywords | ||||
| BENZOXAZIN; Microwave irradiation | ||||
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