Highly Chemoselective Synthesis of 6‐Alkoxy‐1‐alkyl(aryl)‐3‐trifluoroacetyl‐1,4,5,6‐tetrahydropyridines and 1‐Alkyl(aryl)‐6‐amino‐3‐trifluoroacetyl‐1,4,5,6‐tetrahydropyridines

Abstract

AbstractA simple and highly chemoselective method for the synthesis of a large series of novel 6‐alkoxy‐1‐alkyl(aryl)‐3‐trifluoroacetyl‐1,4,5,6‐tetrahydropyridines and 1‐alkyl(aryl)‐6‐amino‐3‐trifluoroacetyl‐1,4,5,6‐tetrahydropyridines, from the reaction of 6‐alkoxy‐3‐trifluoroacetyl‐4,5‐dihydro‐6H‐pyrans with primary alkyl and arylamines, in good yields, is reported. Preliminary in vitro antimicrobial activity of the 1‐alkyl(aryl)‐6‐amino‐3‐trifluoroacetyl‐1,4,5,6‐tetrahydropyridine series was assessed against a variety of microorganisms including yeast‐like fungi, bacteria and algae, and some of these compounds exhibit significant antimicrobial activity.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)