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- Title
De Novo Synthesis of Highly Functionalized Benzimidazolones and Benzoxazolones through an Electrochemical Dehydrogenative Cyclization Cascade.
- Authors
Xu, Fan; Long, Hao; Song, Jinshuai; Xu, Hai‐Chao
- Abstract
Benzimidazolone and benzoxazolone moieties are important scaffolds in a variety of pharmaceutical molecules. These bicyclic heterocycles are usually prepared from a benzene derivative through the construction of an additional five‐membered heterocyclic ring. We report herein a method that enables the efficient synthesis of highly substituted benzimidazolone and benzoxazolone derivatives by building both the benzene and the heterocyclic rings through a dehydrogenative cyclization cascade. Readily available arylamine‐tethered 1,5‐enynes undergo a biscyclization/dehydrogenation cascade to afford functionalized benzanellated heterocycles in a single step with complete control of regioselectivity. These electricity‐powered oxidative transformations proceed with H2 evolution, thus obviating the need for transition‐metal‐based catalysts and oxidizing reagents.
- Subjects
BENZIMIDAZOLES; RING formation (Chemistry); TISSUE scaffolds; HETEROCYCLIC compounds; REGIOSELECTIVITY (Chemistry)
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 27, p9115
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201904931