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- Title
Synthesis of N‐Heterocycles by Dehydrogenative Annulation of N‐Allyl Amides with 1,3‐Dicarbonyl Compounds.
- Authors
Wu, Zheng‐Jian; Li, Shi‐Rui; Xu, Hai‐Chao
- 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.
- Subjects
ANNULATION; HETEROCYCLIC compounds; ALLYL compounds; ELECTROCHEMICAL analysis; PYRROLIDINE derivatives
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 43, p14266
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201807683