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

Authors

  • Л. Г. Воскресенскийr Russian People's Friendship University, Moscow 117198
  • Т. Н. Борисова Russian People's Friendship University, Moscow 117198
  • А. В. Варламов Russian People's Friendship University, Moscow 117198

Keywords:

oxime, pyrrole, pyrrolidine, tetrahydropyrrolo[3,2-c]pyridine, heterocyclization

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.

How to Cite
Voskressensky, L. G.; Borisova, T. N.; Varlamov, A. V. Chem. Heterocycl. Compd. 2004, 40, 326. [Khim. Geterotsikl. Soedin. 2004, 401.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000028629.93231.b8

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Published

2004-03-25

Issue

No. 3 (2004)

Section

Original Papers