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Communication | Regular issue | Vol 32, No. 4, 1991, pp.655-658
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5665
A New Entry to [2.3.4]Cyclazines

Yasuyoshi Miki,* Hiroko Hachiken, Masami Yoshikawa, Shoji Takemura, and Masazumi Ikeda

*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan

Abstract

Treatment of 2,3-dihydro-2-methyl-3-phenyl-1H-pyrazino[3,4,5-cd]indolizine 2-oxides (5) with trifluoroacetic anhydride gave new heterocyclic six-membered betaines (6) which underwnet 1,3-dipolar cycloaddition reaction with dimethyl acetylenedicarboxylate and maleimides in hot toluene to yield the corresponding cycloadducts (7) and (8). Treatment of the maleimide adducts (8) with p-toluenesulfonic acid in boiling acetic acid gave the [2.3.4]cyclazines (9).