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A steroidal‐based synthetic protocol has been developed for the synthesis of substituted steroidal pyridones in the presence of L‐proline. A wide variety of steroidal pyridones were synthesized in better yields. Initially, steroidal benzylidenes were prepared by the aldol condensation of pregnenolone with various substituted aromatic aldehydes under basic conditions. After that heterocyclization of resulting benzylidenes with cyanoacetamide in the presence of L‐proline gives the desired products. With the mild reaction conditions, good conversions, operational simplicity, and inexpensive and readily available catalyst, it is a practical and appealing approach for pyridone synthesis. Structural and quantum chemical insights of synthesized steroidal pyridone derivatives have been also presented using the density functional theory (DFT) approach.

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