REACTIONS WITH NAPATHOYLHYDROXIMOYL CHLORIDES - SYNTHESIS OF DERIVATIVES OF ISOXAZOLE, PYRROLIDINO[3,4-D]ISOXAZOLIN-4,6-DIONE, IMIDAZO[1,2-A]PYRIDINE, IMIDAZO[1,2-A]PYRIMIDINE, BENZOTRIAZINE AND BENZOTHIADIAZINE

摘要

Hydroximoyl chlorides 3 react with acrylonitrile, N-arylmaleimide and maleic anhydride to give isoxazolines 5, pyrrolidino[3,4-d]isoxazolines 8, and furolidino[3,4-d]isoxazolines 9, respectively. 3 reacted with 2-aminopyridine, 2-aminopyrimidine, o-phenylenediamine and o-aminothiophenol to yield 3-nitrosoimidazo[1,2-a]pyridines 20, 3-nitrosopyrimidines 22, 3-naphthoyl-1,4-dihydrobenzo- 1,2,4-triazines 24, and 3-naphthoyl-4H-1,3,4-benzothiadiazine 27, respectively. Compound 3 reacted with benzoylacetonitrile, acetoacetanilide, thiophenol, benzenesulfinic acid in ethanolic sodium ethoxide solution to give the corresponding isoxazoles 12-13 and oximes 16-17, respectively. The structures of these products were confirmed by elemental analyses, spectral data and, wherever possible, alternative synthesis. [References: 14]