Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Dioxopyrrolines. XXXV. Synthesis of 2H-Azepin-2-ones (2-Azatropones)
TAKEHIRO SANOYOSHIE HORIGUCHIKAZUHIKO TANAKAYOSHISUKE TSUDA
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1985 Volume 33 Issue 12 Pages 5197-5201

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Abstract
Eliminative ring expansion of 4-acetoxy (or mesyloxy)-2-azabicyclo [3.2.0] heptan-3-ones (7) yielded 1, 5-dihydro-2H-azepin-2-ones (dihydro-2-azatropones) which, on DDQ oxidation, afforded the 2H-azepin-2-ones (2-azatropones, 9). In contrast to azatropolones, the 2-azatropones were stable to protic solvents. However, irreversible solvolytic changes were observed in both acidic and basic media.
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© The Pharmaceutical Society of Japan
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