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Communication | Special issue | Vol 66, No. 1, 2005, pp.175-179
Published online, 18th November, 2005
DOI: 10.3987/COM-05-S(K)70
1,3-Dipolar Cycloaddition of Ethyl 2,3-Pentadienoate with Pyridinium Dicyanomethylides: Regiospecific Formation of Ethyl 3-Cyano2-ethylindolizine-1-carboxylates and a Novel Formation of Tricyclic Compounds

Naoto Hayashi, Naoto Kawajiri, Takane Uchida, and Kiyoshi Matsumoto*

*Faculty of Pharmaceutical Sciences, Chiba Institute of Science, 3 Shiomi-cho, Choshi, Chiba 288-0025, Japan


Pyridinium dicyanomethylides underwent site- and regioslective 1,3-dipolar cycloaddition with ethyl 2,3-pentadienoate to give ethyl 3-cyano-2-ethylindolizine-1-carboxylates in moderate yields. In two cases, a novel type of the tricyclc compounds, in addition to indolizines, were obtained whose structure was established by a single crystal X-Ray analysis. A plausible mechanism for its formation is also presented.