A SYNTHESIS OF TRIACETYL-SUBSTITUTED 1,2,3,4-TETRAHYDROPYRIDINE BY THE REACTION OF 3-[(ALKYLSULFANYL)METHYL]PENTANE-2,4-DIONES WITH ANILINE

Authors

  • Larisa А. Baeva Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054
  • Rail R. Gataullin Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054
  • Radik M. Nugumanov Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

Keywords:

3-[(alkylsulfanyl)methyl]pentane-2,4-dione, 1,2,3,4-tetrahydropyridine, aniline, cyclization, β-enaminone, [4+2] cycloaddition

Abstract

The condensation of 3-[(alkylsulfanyl)methyl]pentane-2,4-diones with aniline in the presence of catalytic amounts of acetic acid led to the formation of 1,1',1''-(6-methyl-1-phenyl-1,2,3,4-tetrahydropyridine-3,3,5-triyl)triethanone. The reaction is presumably a tandem process, incorporating the formation of β-enaminone, elimination of the alkanethiol molecule from the β-enaminone and the starting pentane-2,4-dione, and a subsequent [4+2] cycloaddition of the resulting intermediates. The mechanism of the conversion may also involve intramolecular cyclization of the Michael addition products of 3-[(alkylsulfanyl)methyl]pentane-2,4-dione to 3-(imidoyl)but-3-en-2-one, formed from β-enaminones during the elimination of alkanethiols.

Author Biographies

Larisa А. Baeva, Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

Лариса Асхатовна

лаборатория химической кинетики, ст.н.с., доцент

Rail R. Gataullin, Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

Раил Рафкатович Гатауллин

лаб. фармакофорных циклических систем, в.н.с., д.х.н.

Radik M. Nugumanov, Ufa Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa 450054

Радик Маратович Нугуманов

лаборатория химической кинетики, м.н.с.

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Published

2024-03-26

Issue

Vol. 60 No. 1/2 (2024)

Section

Short Communications