Reaction of 3-Arylaminobenzofuro-, 3-Arylaminobenzothieno-, and 3-Arylaminoindolo[2,3-c]pyrylium Salts with Nucleophilic Reagents
摘要
We have studied the reactions of 3-arylaminobenzofuro-, 3-arylaminobenzothieno-, and 3-arylaminoindolo[2,3-c]pyrylium salts with ammonium acetate, primary amines, and hydrazine hydrate. In an alcoholic medium, primary amines and hydrazine hydrate open up the pyrylium ring to form arylamides of 2-(N-benzylmethylketimine)hetaryl-3-acetic acids or the corresponding hydrazones, where further heterocyclization does not occur. Upon treatment with ammonium acetate in acetic acid, 2-aryl-1-methylhetero[2,3-c]pyridin-3-(2H)-ones are formed along with their 2-unsubstituted analogs.