What question did this study set out to answer?

To develop a synthesis method for functionalized 1,2,3,4-tetrahydropyridines using anilines and 3-[(propan-2-ylsulfanyl)methyl]pentane-2,4-dione.

February 28, 2026

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

Key Points

To develop a synthesis method for functionalized 1,2,3,4-tetrahydropyridines using anilines and 3-[(propan-2-ylsulfanyl)methyl]pentane-2,4-dione.
Utilized 3-[(propan-2-ylsulfanyl)methyl]pentane-2,4-dione as a reactant
Reacted with various substituted anilines
Employed catalytic amounts of acetic acid
Successfully synthesized 1,1,1-(6-methyl-1-aryl-1,2,3,4-tetrahydropyridine-3,3,5-triyl)triethanolines
Observed variations in reactivity based on the nature and position of substituents on anilines
Identified a specific reactivity order among different aniline substituents.

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)methylpentane-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-Me-CHNH CHNH = 4-Me-CHNH = 2-Me-CHNH 3-Me-CHNH = 2-MeO-CHNH 4-MeC(O)-CHNH = 4-Br-CHNH.

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L. A. Baeva

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

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