Five-Membered 2, 3-Dioxo Heterocycles: L. Synthesis and Thermolysis of 3-Aroyl-and 3-Hetaroyl-5-phenyl-1, 2, 4, 5-tetrahydropyrrolo [1, 2-a] quinoxalin-1, 2, 4- …

KS Bozdyreva, IV Smirnova, AN Maslivets

Index: Bozdyreva; Smirnova; Maslivets Russian Journal of Organic Chemistry, 2005 , vol. 41, # 7 p. 1081 - 1088

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Citation Number: 14

Abstract

Abstract (Z)-3-Phenacylidene-and (Z)-3-hetaroylmethylidene-1-phenyl-1, 2, 3, 4- tetrahydroquinoxalin-2-ones react with oxalyl chloride to give 3-acyl-5-phenyl-1, 2, 4, 5- tetrahydropyrrolo [1, 2-a] quinoxaline-1, 2, 4-triones. Thermolysis of the latter generates acyl (3-oxo-4-phenyl-3, 4-dihydroquinoxalin-2-yl) ketenes which are stabilized via [4+ 2]- cyclodimerization followed by [1, 3]-acylotropic shift to afford 4-acyl-3-acyloxy-2-(3-oxo-4- ...