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-triones

(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. V Thermolysis of the latter generates acyl(3-oxo-4-phenyl-3,4-dihydroquinoxalin-2-yl)keten...

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Bibliographic Details
Published inRussian journal of organic chemistry Vol. 41; no. 7; pp. 1081 - 1088
Main Authors Bozdyreva, KS, Smirnova, Maslivets, AN
Format Journal Article
LanguageEnglish
Published NEW YORK Springer Nature 01.07.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
2,3-DIOXOHETEROCYCLES
1-ARYL-4-AROYL-5-METHOXYCARBONYL-2,3-DIHYDRO-2,3-PYRROLEDIONES
WATER
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Summary:(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. V 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-oxo4-phenyl-3,4-dihydroquinoxalin-2-yl)-6-phenyl-5,6-dihydro-1H-pyrido[1,2-a]quinoxaline-1,5-diones.
ISSN:1070-4280
1608-3393
DOI:10.1007/s11178-005-0296-6