Synthesis and comparative study of reactivities of δ-lactone,estor group and oxazinone ring in coumarin derivatives towards carbon or nitrogen nucleophiles  

作　　者：EL-KAFRAWY,A.F. SOLIMAN,A.Y. BAKER,H.M. MOHAMED,F.K. EL-KADY,M.Y.Department of Chemistry,Faculty of Science,Ain Shams University and Faculty of Education at El-Fayoum,Cairo.Egypt 

出　　处：《Chinese Journal of Chemistry》1990年第5期469-473,共2页中国化学（英文版）

摘　　要：Condensation of methyl 7-methylcoumarin-4-acetate(2)with primary amines and with an- thranilic acid gave 7-methyl-2-oxo-N-aryl-2H-[1]-benzopyran-4--acetamide(4a—d)and(7),respectively. Compound 7 underwent cyclization to give 2-(7-methyl-2-oxo-2H-[1]-benzopyran-4-yl)-methyl-4H-3,1- benzoxazin-4-one(3).The reaction of 3 with aromatic amines gave the corresponding quinazolone derivatives 5 which tautomerises to the thermodynamically more stable isomer 6,whereas its reaction with Grignard reagents and aromatic aldehydes gave 8a,8b,and 9a,9b,respectively.Condensation of methyl 7-methylcoumarin-4-acetate(2)with primary amines and with an- thranilic acid gave 7-methyl-2-oxo-N-aryl-2H-[1]-benzopyran-4--acetamide(4a—d)and(7),respectively. Compound 7 underwent cyclization to give 2-(7-methyl-2-oxo-2H-[1]-benzopyran-4-yl)-methyl-4H-3,1- benzoxazin-4-one(3).The reaction of 3 with aromatic amines gave the corresponding quinazolone derivatives 5 which tautomerises to the thermodynamically more stable isomer 6,whereas its reaction with Grignard reagents and aromatic aldehydes gave 8a,8b,and 9a,9b,respectively.

关 键 词：Synthesis and comparative study of reactivities of lactone estor group and oxazinone ring in coumarin derivatives towards carbon or nitrogen nucleophiles RING 

分 类 号：O6[理学—化学]