M. M. Kandeel
Jan 1, 2000
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Journal
Phosphorus, Sulfur, and Silicon and the Related Elements
Abstract
Abstract 2-(2-thioxo-4-oxo-thiazolidin-3-yl-)-6-(4-nitrophenylthio)-benzthiazole 1was prepared and condensed with two moles of aromatic amine to give the corresponding 2,4-diarylimino thiazolidines 2 a-b. The latter compounds undergo cycloaddition reaction with chloroacetylchloride and thioglycolic acid to give spiro compounds 5 a-b and 6 a-b The reaction of 1 with hydrazine hydrate afforded 2-hydrazono compound 3. Reaction of 3 with phenyl isothiocyanate gave the corresponding thiosemicarbazone 9. Cyclocondensation of chloroacetic acid with 9 afforded compound 10. Also, condensation of 3 with aromatic aldehydes gave the corresponding Schiff's bases 11 a-c. Reaction of compound 1 with malononitrile gave compound 4 which was reacted with sulfur in presence of diethylamine to give thienothiazole derivative 14. Compound 4 was reacted also with carbon disulfide in presence of triethylamine to afford thiopyranthione 15. Furthermore, the active methylene of 4 couples with benzene diazonium chloride followed by cyclization to give thiazolopyridazine derivative 17. Oxidation of compounds 5 a-b, 6 a-b, 10, 11 a-c, 14, 15 and 17 using H2O2/ACOH mixture afforded the corresponding diarylsulfones 7 a-b, 8 a-b, 12, 13 a-c, 18, 19 and 20.