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J Org Chem ; 82(24): 13700-13707, 2017 12 15.
Artigo em Inglês | MEDLINE | ID: mdl-29131628

RESUMO

This work reports the design of [1,3,4]thiadiazolo[3',2':1,2]imidazo[4,5-c]quinolines using a Pictet-Spengler reaction. The scope of the reaction was achieved from 6-(2-aminophenyl)imidazo[2,1-b][1,3,4]thiadiazole derivatives and available aldehydes. A wide range of aldehydes were employed to examine the scope of the cyclization. In parallel, a mechanism investigation was realized and showed a hydride transfer which led to a dismutation of the intermediate species. To complete this methodological study, a "sequential" oxidation/SNAr procedure was performed to achieve C-2 nucleophilic substitution using several amine types.

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