Influence of Substituents on the Reaction of Substituted (4‐Oxo‐3‐Phenyl‐1,3‐Thiazolidin‐2‐Ylidene)acetates with α,α‐Dicyanoolefins: Synthesis of Quinoline and Quinazoline‐Substituted Carboxylates

Abstract

AbstractIn this work, a novel strategy for the straightforward synthesis of quinoline and quinazoline‐substituted carboxylates is described. The reaction between substituted (4‐oxo‐3‐phenyl‐1,3‐thiazolidin‐2‐ylidene)acetates and substituted α,α‐dicyanoolefins is explored, with a focus on the effects of substituents. The process involves a base‐mediated Michael addition, cleavage of C−C bonds, intramolecular cyclization, [1,5]‐H shift, and aromatization. The benefits of this process include high efficiency, mild reaction conditions, simplicity, and a wide range of products. To the best of our knowledge, there are no previous reports for the synthesis of these classes of quinoline and quinazoline‐substituted carboxylate derivatives.