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Base induced chemical conversion of 3-carbamoyl-2-isoxazolines
Nagatoshi Nishiwaki1, Asaka Maki, Masahiro Ariga
1Center for Collaborative Research, Anan National College of Technology, Tokushima 774-0017, Japan. nishiwaki@anan-nct.ac.jp
Abstract:
3-Carbamoyl-2-isoxazolines, prepared by cycloaddition of functionalized nitrile oxide, serve as masked 3-unsubstituted isoxazolines to afford 2-isoxazoline-3-carboxylic acid, beta-cyanoalcohol, alpha,beta-unsaturated nitrile, and alpha,beta-unsaturated amide upon heating in the alkaline solution. The present reaction is also applicable to synthesis of 3,4-difunctionalized isoxazoles and beta-hydroxy-gamma-lactone.
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