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Updated: Jun 3, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Aza-annulation on the 16-dehydropregnenolone, via tandem intermolecular aldol process and intramolecular Michael
Manmeet Kumar1, Preeti Rawat, Mohammad Faheem Khan
1Medicinal and Process Chemistry Division, Central Drug Research Institute, CSIR, Lucknow 226 001, India.
Abstract:
16-Dehydropregnenolone undergoes a smooth annulation with propan-1-amine and aromatic aldehydes. Several amine derivatives of 16- dehydropregnenolone were synthesized and evaluated as inhibitors of DPP-IV. The structures of compounds were confirmed by (1)H, (13)C, NMR and mass spectral analysis. Among 17 compounds evaluated only five compounds 1, 9, 13, 15 and 16 demonstrated significant inhibition of DPP. This study suggest that introduction of appropriate substituents in the 16-dehydropregnenolone plays an important role in DPP-IV inhibitory activity.
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