Journal article
One-Pot Syntheses of Substituted Oxazoles and Imidazoles from the Isocyanide Asmic
Journal of organic chemistry, v 88(2), pp 909-916
20 Jan 2023
PMID: 36598123
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
Substituted oxazoles and imidazoles are synthesized in one pot from the isocyanide building block Asmic (anisylsulfanylmethyl isocyanide), an alkyl halide, and an acid chloride or nitrile, respectively. The modular assembly employs sequential deprotonation-alkylation and deprotonation-acylation or imination of Asmic, followed by an unusual carbon-sulfur bond cleavage to construct the azole. The strategy is robust, highly efficient, and affords C4-C5 disubstituted oxazoles or imidazoles in a single operation
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Details
- Title
- One-Pot Syntheses of Substituted Oxazoles and Imidazoles from the Isocyanide Asmic
- Creators
- Louis G. Mueller Jr - Johns Hopkins Drug Discovery, Baltimore, MD 21205 USATaylor M. Keller - University of PennsylvaniaFraser F. Fleming - Drexel University
- Publication Details
- Journal of organic chemistry, v 88(2), pp 909-916
- Publisher
- American Chemical Society; Washington, DC
- Number of pages
- 8
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000909525800001
- Scopus ID
- 2-s2.0-85145988361
- Other Identifier
- 991020898396304721
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- Collaboration types
- Domestic collaboration
- Web of Science research areas
- Chemistry, Organic