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

A 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-amino3-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 I-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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)