6582-80-5Relevant academic research and scientific papers
Synthesis and antimicrobial activity of arylazoenamines
Boido,Boido,Sparatore,Sparatore,Bombieri,Benetello,Debbia,Schito
, p. 749 - 775 (2007/10/02)
The possibility to obtain new arylazoenamines endowed with antifungal activity was examined by reacting with acids the arylhydrazones of several keto- and aldo-tert. amines as dimethyl-3-aminoacetone, 3-quinuclidinone, 1-methyl-3-piperidone and 2-formyl-1-methylpyrrolidine. The reaction was successful only in the last two cases. From each 1-methyl-3-piperidone arylhydrazone two isomeric arylazoenamines were formed, which were identical with those obtained from the analogous arylhydrazone of 2-formyl-1-methylpyrrolidine. The structure of these compounds was settled on the ground of UV, IR, NMR and mass spectra and confirmed by means of X-ray analysis. A mechanism is proposed for the formation of arylazoenamines through the contraction of piperidine ring and enlargement of the pyrrolidinic one. The prepared compounds [3-arylazo-1-methyl-Δ2-piperidines 17 and 1-methyl-2(arylazo)methylene pyrrolidines 18] exhibited only a very weak antibacterial activity, but were moderately active against several Candida species and other yeast-like fungi.
