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Heterocyclization of Oximes of 3,5-Dimethyl(1,3,5-trimethyl)-2,6-diphenylpiperid-4-ones and N-Benzylpyrrolid-3-ones with Acetylene in a Superbasic Medium

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It has been established that on heterocyclization of 3,5-dimethyl-2,6-diphenylpiperid-4-one oxime with acetylene in a superbasic medium migration of the 3a-CH3 group to the anionic nitrogen atom occurs, leading to the formation of 5,7-dimethyl-4,6-diphenyl-4,5,6,7-tetrahydropyrrolo[3,2-c]pyridine. The formation of the N-anion causes aromatization of the tetrahydropyridine ring. Tetrahydropyrrolo[1,2-c]pyrimidines are formed in the Trofimov reaction as a result of decomposition of the intermediate 3H-pyrrole in a retro-Mannich reaction.

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  1. Russian People's Friendship University, Moscow, 117198

    L. G. Voskressensky, T. N. Borisova & A. V. Varlamov

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  1. L. G. Voskressensky
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  2. T. N. Borisova
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  3. A. V. Varlamov
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Voskressensky, L.G., Borisova, T.N. & Varlamov, A.V. Heterocyclization of Oximes of 3,5-Dimethyl(1,3,5-trimethyl)-2,6-diphenylpiperid-4-ones and N-Benzylpyrrolid-3-ones with Acetylene in a Superbasic Medium. Chemistry of Heterocyclic Compounds 40, 326–333 (2004). https://doi.org/10.1023/B:COHC.0000028629.93231.b8

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  • DOI: https://doi.org/10.1023/B:COHC.0000028629.93231.b8

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