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Paper | Regular issue | Vol 41, No. 10, 1995, pp.2181-2188
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7084
Formation of Dihydroaza-azulanones Possessing Spirocyclic Moieties: [8+2] Type Cycloaddition Reactions of Iminotropones to an Exocyclic Double Bond of 8-Oxoheptafulvene

Yuka Saito, Masayuki Tomita, Hiroshi Taniguchi, Hirofumi Okabayashi, and Katsuhiro Saito*

*Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466, Japan

Abstract

Reactions of N-(p-substituted phenyl) iminotropones with 8-oxoheptafulvene proceeded through [8+2] type cycloadditions to form dihydroaza-azulanones possessing spirocyclic and norcaradiene moieties. Reactions of 8-oxoheptafulvene with phenyl- or tosylhydrazones of tropone gave the same type of dihydroazaazulanones. Analogous reactions with N-alkyliminotropone N-oxides also gave the same type of adducts via the corresponding N-alkyliminotropones, which were derived from reactions of the iminotropone N-oxides with 8-oxoheptafulvene.