Abstract
A one-pot synthesis of N-substituted azepines under aqueous conditions is described. The synthesis of several azepines derivatives was carried out by reaction of 2,5-dimethoxytetrahydrofuran, aromatic amines and dimethyl/diethyl acetylene dicarboxylate in the presence of CsI in water at ambient temperature. Products were obtained in high yields and catalyst was recovered and reused without a significant decrease in catalytic activity.
Keywords
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