Synthesis of new 4-methyl-2-(4-pyridyl)-1,2,3,4-tetrahydroquinolines as potent antifungal compounds

Abstract

A síntese, a caracterização espectroscópica e os resultados biológicos de novas séries de 2-(4-piridil)-1,2,3,4-tetrahidroquinolinas e seus precursores, -N-aril-N-[1-(4-piridil)but-3-enil] aminas, são descritos. Foi encontrado que ambos, precursores substituídos g-piridil e os produtos finais, as tetrahidroquinolinas, demonstraram excelentes atividades antifúngicas contra

Progress in the Chemistry of Tetrahydroquinolines

“…Thus, Kouznetsov and co-workers synthesized homoallylamines 230 via the Grignard reaction of aldimines 229 with allyl magnesium bromide or using the Barbier reaction of the same aldimines with allyl bromide in the presence of powdered indium (Scheme ). Compounds 230 were converted into 1,2,3,4-tetrahydroquinolines 231 by treatment with sulfuric acid at 80–90 °C. The α-pyridyl-substituted tetrahydroquinolines 231 thus obtained, and also the corresponding homoallylamines 230 , showed good antifungal activities.…”

Advances in the Chemistry of Tetrahydroquinolines

“…The Povarov reaction, which will be discussed in section in detail, was also employed for the construction of the tetrahydroquinoline ring. A similar approach was also used for the synthesis of simple antifungal 1,2,3,4-tetrahydroquinolines ,, and 2-spirotetrahydroquinolines …”

Titanocene(III) Chloride Mediated Radical Induced Allylation of Aldimines: Formal Synthesis of C-Linked 4′-Deoxy Aza-disaccharide

“…Homoallyl amines proved to be eminent building units for the asymmetric synthesis of pyrrolidines and piperidines via a ring-closing metathesis (RCM) . Moreover, it has also been assayed that homoallyl amines containing aryl rings at C-4 of butene moiety exhibit considerable antimicrobial activity against some infective dermatophytes …”