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Synthesis of N‐Heterocycles by Dehydrogenative Annulation of N‐Allyl Amides with 1,3‐Dicarbonyl Compounds
Author(s) -
Wu ZhengJian,
Li ShiRui,
Xu HaiChao
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201807683
Subject(s) - annulation , chemistry , oxidizing agent , pyrrolidine , reagent , catalysis , combinatorial chemistry , organic chemistry , malonate , medicinal chemistry
Abstract Dehydrogenative annulation under oxidizing reagent‐free conditions is an ideal strategy to construct cyclic structures. Reported herein is an unprecedented 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, which obviates the need for oxidizing reagents and transition‐metal catalysts. In these reactions, the N‐allyl amides serve as a four‐atom donor to react with dimethyl malonate to give pyrrolidines by a (4+1) annulation, or with β‐ketoesters to afford tetrahydropyridine derivatives by a (4+2) annulation.