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Communication | Regular issue | Vol 2, No. 5, 1974, pp.575-584
Published online, 1st January, 1970
DOI: 10.3987/R-1974-05-0575
The Rection of 1-(1-Pyrrolidinyl)cyclohexene with Pyrrole and Pyrazole

Masashi Tashiro, Yoko Kiryu, and Otohiko Tsuge*

*Research Institute of Industrial Science, Faculty of Engineering, Kyushu University, 6-1, Kasuga-koen, Kasuga 816-8580, Japan


Michael type adducts of pyrrole (2) and pyrazole (2) to enamine (1), 4 and 5, decompose at elevated temperature to regenerate 1 and 2 or 3. On prolonged heating of 4, the novel hexahydro-4H-pyrrolo[1,2-a]indole-4-spiro-1’-cyclohexane derivative (8) was obtained along with four cyclohexenyl-substituted pyrroles, 6a, 6b, 7a, and 7b. The reaction of 1 with 2 under forcing conditions directly afforded 6, 7, and 8, whose relative amounts depended on the reaction conditions. On the other hand, both the thermal decomposition of 5 and the reaction of 1 with 3 under forcing conditions gave 4-(1-cyclohexenyl)pyrazole (13) as a sole isolated product.