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Communication | Regular issue | Vol 22, No. 10, 1984, pp.2199-2202
Published online, 1st January, 1970
DOI: 10.3987/R-1984-10-2199
Cycloaddition Reactions of Xanthinium N(7)-Ylides with Trans Olefinic Dipolarophiles

Mikio Hori,* Tadashi Kataoka, Hiroshi Shimizu, Eiji Imai, Yukiharu Matsumoto, Masanori Kawachi, Kazuyoshi Kuratani, Haruo Ogura, and Hiroaki Takayanagi

*Department of Pharmacognosy, Gifu College of Pharmacy, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

The xanthinium N(7)-ylides reacted with olefinic dipolarophiles to give tetrahydropyrrolo[1,2-f]xanthine derivatives. Reaction with dimethyl fumarate gave the mixture of endo and exo adducts. The stereochemistry of these products was elucidated by 1H-NMR and X-ray analysis. Reaction with other trans olefins afforded solely endo-syn type addition products in excellent yields.