Synthesis of biologically active thiazolo-benzopyranyl-<i>s</i>-triazine derivatives

Abstract

621-6266-Amino-2-oxo-2H [1]-benzopyran on oxidative cyclisation with potassium thiaocynate, acetic acid and bromine at 0-5°C gives 2-amino-7H [6]- thiazolo [5,4-d] benzopyran-7-one 1, which on treatment with cyanuric chloride in alcohol gives 2-(2'-amino-7'-oxo-7' H [6']- thiazolo [5', 4'-d] benzopyranyl)-4-6-dichloro-s-triazine 2. 6-Amino-2-oxo-2H [1]-benzopyran on refluxing with ammonium thiocynate in hydrochloric acid and ethanol gives 6-thioureido-2H [1]-benzopyran-2-one 3. Compound 2 on refluxing with 3 in alcohol gives 2-(2'-amino-7'-oxo-7'H [6']- thiazolo [5', 4'-d] benzopyranyl)-4-(6"thioureido-2" H-[1"]-2" -oxo-benzopyranyl)-6-chloro-s-triazine 4. The similar reaction is repeated on 4 to give 2-(2'-amino-7' -oxo-7' H [6']- thiazolo [5', 4'-d] benzopyranyl)-4-(6"-thioureido-2" H [1"]-2"-oxo benzopyranyl)-6-(6'" -thioureido-2'" H[1"']-2'" -oxo-benzopyranyl)-s-triazine 5. The structures of all compounds are confirmed on the basis of analytical and spectral data. Some of the compounds show significant antibacterial activity