A Synthesis of Functionalized 1,2,3,4-Tetrahydropyridines by the Reaction of 3-[(Propan-2-ylsulfanyl)Methyl]Pentane-2,4-Dione with Anilines

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Abstract

A method for the synthesis of 1,1,1-(6-methyl-1-aryl-1,2,3,4-tetrahydropyridine-3,3,5-triyl)triethanolines was developed by the reaction of 3-[(propan-2-ylsulfanyl)methyl]pentane-2,4-dione with anilines in the presence of catalytic amounts of acetic acid. The reactivity of substituted anilines in the studied reaction, depending on the nature and position of the substituent, decreases in the series: 2,4-Me2-C6H3NH2 > C6H3NH2 = 4-Me-C6H4NH2 = 2-Me-C6H4NH2 > 3-Me-C6H4NH2 = 2-MeO-C6H4NH2 > 4-MeC(O)-C6H4NH2 = 4-Br-C6H4NH2.

About the authors

L. A. Baeva

Ufa Institute of Chemistry, Ufa Federal Researcher Centre of the Russian Academy of Sciences

Email: sulfur@anrb.ru
ORCID iD: 0000-0002-4475-8556
Ufa, Russia

R. M. Nugumanov

Ufa Institute of Chemistry, Ufa Federal Researcher Centre of the Russian Academy of Sciences

ORCID iD: 0000-0001-8649-2680
Ufa, Russia

R. R. Gataullin

Ufa Institute of Chemistry, Ufa Federal Researcher Centre of the Russian Academy of Sciences

ORCID iD: 0000-0003-3269-2729
Ufa, Russia

T. R. Nugumanov

Ufa Institute of Chemistry, Ufa Federal Researcher Centre of the Russian Academy of Sciences

ORCID iD: 0000-0003-3355-7262
Ufa, Russia

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