Synthesis of Several New Isoxazole, Imidazo[1, 2-a]pyridine, Imidazo[1, 2-a]pyrimidine, Benzoxadiazine and Benzothiazine Derivatives from Hydroximoyl Halides

Furoyldroximoyl chloride 3d reacted with 2-aminopyridine, 2-aminopyrimidine. O-aminophenol, O-phenylenediamine and aminothiophenol to afford imidazo [1, 2-a]pyridine 6. imidazo[1, 2-a]pyrimidine 8, benzoxadiazine 10, nitrosobenzopyrizine 13a and nitrosobenzothiazine 13b, respectively. Isoxazoline 18 and pyrrolidino[3, 4-d]isoxazolin-4, 6-dione derivatives 19a and 19b obtained by the reaction of 3 with acrylonitrile and N-arylmaleimide. Hydroximoyl chloride 3 reacted with thiophenol and sodium benzene-sulfinate to yield furylglyoxaloxime 16a and 16b, respectively. Hydroximoyl chloride 3 reacted also with some active methylene compound to give isoxazole derivatives 20-23, respectively.