An iron-catalyst mediated one-pot multicomponent route for the synthesis of novel 6-thioxo-hexahydroindeno[1′,2′:4,5]imidazo[1,5-a]pyridin-12(6H)-one scaffolds has been developed using ninhydrin, L-proline, and aryl isothiocyanates in ethanol medium. This methodology offers an interesting [1,2] oxygen shift mechanism pathway via a number of ring-opening and ring-closing cascade steps to provide diverse substituted hexahydroindeno-imidazo[1,5-a]pyridinones in excellent to good yields. The stereochemistry of the proline ring is lost during the course of the reaction. This protocol is well acceptable toward both electron-accepting and electron-donating functionalities at the ortho-, meta-, and para-positions of the isothiocyanate moiety. Nonhazardous conditions, step economic, and easy operational process are the advantages of this methodology.

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