Furan derivatives. Part 10. Synthesis of cyclohepta [cd] benzofuran

T Horaguchi, E Hasegawa, T Shimizu…

Index: Horaguchi, Takaaki; Hasegawa, Eietsu; Shimizu, Takahachi; Tanemura, Kiyoshi; Suzuki, Tsuneo Journal of Heterocyclic Chemistry, 1989 , vol. 26, p. 365 - 369

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Citation Number: 12

Abstract

Abstract Cyclohepta [cd] benzofuran 2 was synthesized by heating (5-oxo-5H- benzocyclohepten-4-yloxy) acetic acid 16 with sodium acetate in acetic anhydride or by photocyclization of 16 in acetonitrile. Several reactions of cyclohepta [cd] benzofuran 2 were examined. Protonation of 2 with trifluoroacetic acid occurred at the 2-position to give a tropylium ion 17. Catalytic hydrogenation of 2 with palladium on charcoal proceeded ...