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Communication | Regular issue | Vol 20, No. 6, 1983, pp.1009-1012
Published online, 1st January, 1970
DOI: 10.3987/R-1983-06-1009
1,3-Dipolar Cycloaddition of Pyridinium and Diazinium Dicyanomethylids with Bis(trimethylsilyl)acetylene: Synthesis of Trimethylsilyl Substituted Indolizines and Bis(trimethylsilyl)acetylene as an Acetylene Equivalent in 1,3-Dipolar Cycloaddition

Yukio Ikemi, Kiyoshi Matsumoto, and Takane Uchida

*Graduate School of Human and Environmental Studies, Kyoto University, Yoshida-Nihonmatsu-cho, Sakyo-ku, Kyoto 606-8501, Japan


Cycloaddition reactions of pyridinium and diazinium dicyanomethylids with bis(trimethylsilyl)acetylene give either the corresponding 1,2-di(trimethylsilyl)-3-cyanoindolizines or the mixtures of these and 1-(trimethylsilyl)-3-cyanoindolizines depending on the substituents and the presence of another nitrogen in the pyridine ring. The trimethylsilyl group was smoothly removed under the catalytic influence of (n-Bu)4NF.