Nucleophilic reactions on 1-trifluoromethanesulfonylpyridinium trifluoromethanesulfonate (triflylpyridinium triflate, TPT). Ring-opening and 'unexpected' 1,4-dihydropyridine reaction products

Autor:	Carlos F. Amábile-Cuevas, Raúl Ponce Rosas, Federico del Rio Portilla, Olivia Garcia-Mellado, Cecilio Alvarez-Toledano, Rubén A. Toscano, María del Carmen Hernández-Galindo
Předmět:	Nucleophilic addition General Chemistry General Medicine Ring (chemistry) Chemical synthesis Medicinal chemistry chemistry.chemical_compound chemistry Nucleophile Drug Discovery Pyridinium Cyanine Trifluoromethanesulfonate Antibacterial agent
Zdroj:	Web of Science Scopus-Elsevier
Popis:	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 (I-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.
Databáze:	OpenAIRE
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