Rearomatization of trifluoromethyl sulfonyl dihydropyridines: Thermolysis vs photolysis

FIRPO, GUADALUPE; COOKE, MARÍA V.; PELÁEZ, WALTER J.; CHANS, GUILLERMO M.; ARGÜELLO, GUSTAVO A.; GÓMEZ, ELIZABETH; ALVAREZ-TOLEDANO, CECILIO

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY

JOHN WILEY & SONS LTD

Año: 2017 p. 1 - 1

0894-3230

n this article, we describe the static gas‐phase pyrolysis, microwave‐inducedpyrolysis, and photolysis reactions of trifluoromethyl sulfonyl dihydropyridines.The goal of this work was to find a methodology that allows obtaining ofsubstituted pyridines?which are known to be difficult to synthesize?to bereused in a new substitution reaction. We demonstrated that it is possible toachieve the rearomatization process by the elimination of the trifluoromethylsulfonyl moiety through the 3 processes, with the static pyrolysis being the bestmethod to obtain the substituted pyridines. In addition, we propose the 1,4‐elimination (CF3SO2 + H) as the first step, since it is the less energetic process,as has also been corroborated by calculations. A competitive reaction (CO2extrusion) also occurs, yielding undesired products.