Title: Synthesis of N‐Heterocycles via Dehydrogenative Annulation of N‐Allyl Amides with 1,3‐Dicarbonyl Compounds

Author: Zheng-Jian Wu  Shi-Rui Li  Hai-Chao Xu

Abstract:

Dehydrogenative annulation under oxidizing reagent‐free conditions is an ideal strategy to construct cyclic structures. Herein we report an unprecedented method for the synthesis of pyrrolidine and tetrahydropyridine derivatives through electrochemical dehydrogenative annulation of N‐allyl amides with 1,3‐dicarbonyl compounds. The electrolytic method employs an organic redox catalyst and obviates the need for oxidizing reagents and transition‐metal catalysts. In these annulation reactions, the N‐allyl amides serve as a four‐atom donor to react with dimethyl malonate to give pyrrolidines via (4+1) annulation or with β‐ketoesters to afford tetrahydropyridine derivatives via (4+2) annulation.

Full-Link: https://onlinelibrary.wiley.com/doi/10.1002/anie.201807683