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Reactions of cyclic oxalyl compounds, 43: Synthesis and thermolysis of fused 1-arylaminopyrrolones

✍ Scribed by Gert Kollenz; Ralph Theuer; Karl Peters; Eva-Maria Peters

Publisher: Journal of Heterocyclic Chemistry
Year: 2001
Tongue: English
Weight: 131 KB
Volume: 38
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570380508

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✦ Synopsis

Abstract

Fused N‐(di)arylamino‐pyrrol‐2,3‐diones 1 are reacted with diphenylketene, thiosemicarbazide or 1,2‐diaminobenzene to afford the 3‐diphenylmethylene pyrrolones 2, the thiosemicarbazones 4 or the quinoxaline derivatives 5 as well as 6, respectively. Thermolysis of 2b,c,e,f,6b and the pyrrolo‐quinoxaline 8 afford the corresponding N‐deaminated products 3, 7 and 9. Rearrangements into diazapropellanes following a thermally initiated Fischer ‐ indolization as originally expected do not occur.

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