Base induced chemical conversion of 3-carbamoyl-2-isoxazolines.
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.
Nishiwaki
Nagatoshi
N
Center for Collaborative Research, Anan National College of Technology, Tokushima 774-0017, Japan. nishiwaki@anan-nct.ac.jp
Maki
Asaka
A
Ariga
Masahiro
M
D000468:Alkalies / Q000737:chemistry*; D003500:Cyclization; D006868:Hydrolysis; D007555:Isoxazoles / Q000737:chemistry*
D000468:Alkalies; D007555:Isoxazoles