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Paper | Special issue | Vol 59, No. 1, 2003, pp.149-160
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S7
Synthesis of Spiro-fused Nitrogen Heterocyclic Compounds via N-Methoxy-N-acylnitrenium Ions Using Phenyliodine(III) Bis(trifluoroacetate) in Trifluoroethanol

Etsuko Miyazawa, Takeshi Sakamoto, and Yasuo Kikugawa*

*Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan

Abstract

Spirodienones and spirodienes bearing the nitrogen atom bound to the spiro carbon have been synthesized from N-methoxy-(4-methoxyphenyl)amides and N-methoxyphenylamides, respectively, by the intramolecular ipso attack of a nitrenium ion generated with phenyliodine(III) bis(trifluoroacetate) in trifluoroethanol.