Synthesis of Functionalized 1,2,3,4-Tetrahydropyridines by the Reaction of 3-[(Propan-2-ylsulfanyl)methyl]pentane-2,4-dione with Anilines

Abstract

A method for the synthesis of 1,1,1-(6-methyl-1-aryl-1,2,3,4-tetrahydropyridine-3,3,5-triyl)triethanones by the reaction of 3-[(propan-2-ylsulfanyl)methyl]pentane-2,4-dione with anilines in the presence of catalytic amounts of acetic acid was developed. It was found that the reactivity of substituted anilines in the studied reaction depends on the nature and position of the substituent, decreasing in the series: 2,4-Me₂-С₆H₃NH₂ > С₆H₅NH₂ 4-Me-С₆H₄NH₂ 2-Me-С₆H₄NH₂ > 3-Me-С₆H₄NH₂ 2-MeO-С₆H₄NH₂ > 4-MeC(O)-С₆H₄NH₂ 4-Br-С₆H₄NH₂.