Nucleophilic Reactions on 1-Trifluoromethanesulfonylpyridinium Trifluoromethanesulfonate (Triflypyridinium Triflate, TPT).Ring-Opening and "Unexpected" 1, 4-Dihydropyridine Reaction Products

Abstract

The reaction products of 1-trifluoromethanesulfonylpyridinium trifluoromethanesulfonate (TPT) with secondary amines have been thoroughly examined by spectroscopic and X-ray diffraction methods. The products include the normal ones expected for a ring-opening reaction (1-azahexatriene and cyanine) in addition to the "unexpected"formation of a 4-substituted 1, 4-dihydropyridine. Tandem reactions -ring-opening, nucleophilic addition- on the pyridinium ring seems to be the most probable pathway to the 1, 4-dihydropyridine compounds. Preliminary tests on the compounds revealed significant anti-microbial activity against Gram-positive bacteria, with moderate specificity towards Enterococcus faecalis.