Regioselective Synthesis of Iminothiazolidinone Appended Novel Dispiro Indenoquinoxaline‐Pyrrolidines by 1,3‐Dipolar Cycloaddition Strategy

Abstract

AbstractA series of structurally fascinating novel dispiroindenoquinoxaline hybrids have been synthesized with complete regio and diastereoselectivity via comprising three pharmocophoric cores, i. e., indenoquinoxaline, pyrrolidine and iminothiazolidinone in a single molecular framework by means of 1,3‐dipolar cycloaddition reaction under microwave irradiations. In the present study azomethine ylide generated in situ by the condensation reaction of indenoquinoxalinone and benzyl amine, which subsequently react with dipolarophile alkyl‐2‐[(Z)‐4‐oxo‐3‐aryl/alkyl‐2‐(arylimino)thiazolidin‐5‐ylidene] acetate to construct iminothiazolidinone appended dispiro‐indenoquinoxaline‐pyrrolidines with unusual regio and endo‐selective manner. The present study involves the generation of three new bonds and more than three stereogenic centers in a single operation under mild reaction conditions with high yields in shorter reaction time. The structure elucidation is based on NMR spectroscopic studies and regio‐/stereochemistry has been concluded by single crystal X‐ray diffraction analysis.