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- Title
Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines.
- Authors
Zhang, Zhen; Huang, Baoliang; Qiao, Guanyu; Zhu, Liu; Xiao, Fan; Chen, Feng; Fu, Bin; Zhang, Zhenhua
- Abstract
Amidine is a notable nitrogen-containing structural motif found in bioactive natural products and pharmaceuticals. Herein, a novel rhodium(I)-catalyzed tandem reaction of readily accessible azides with isonitriles and boronic acids via a carbodiimide intermediate is achieved. This protocol offers an alternative approach toward N-sulfonyl-, N-acyl-, and N- phosphoryl-functionalized, as well as general N-aryl and N-alkyl amidines with broad substrate scope. In addition, functionalized guanidines can also been synthesized when amines are used instead. The accomplishment of estrone-derived amidine and glibenclamide bioisosteres further reveals the practical utility of this strategy.
- Subjects
ORGANIC compounds; BORONIC acids; AMIDINES; RHODIUM; NONCARBOXYLIC acids
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 15, p4384
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201700539