Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Acid-Promoted Multicomponent Tandem Cyclization to Synthesize Fully Substituted Oxazoles via Robinson–Gabriel-Type Reaction

Acid-Promoted Multicomponent Tandem Cyclization to Synthesize Fully Substituted Oxazoles via Robinson–Gabriel-Type Reaction
Rong-Rong Zhou, An-Xin Wu, Deng-Kui Li, Yan-Dong Wu, Qun Cai, Shi-Yi Zhuang
An acid-promoted multicomponent reaction for the synthesis of diverse fully substituted oxazole derivatives from simple and readily available arylglyoxal monohydrates, nitriles, and various C-nucleophiles has been developed. This protocol features wide functional group diversity which is capable of installing 4-hydroxycoumarin, 2-naphthol, and 1,3-cyclohexanedione motifs to oxazoles. Mechanistic analysis indicates that a classical Robinson–Gabriel reaction served as the key step for this tandem transformation.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00763

DOI: 10.1021/acs.joc.7b00763

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