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2-Amino-6-methoxybenzothiazole 1 on reaction with bis(methylthio)methylene malononitrile 2 in the presence of dimethyl formamide and catalytic amount of anhydrous potassium carbonate afforded 3-cyano-4-imino-8-methoxy-4H-pyrimido[2,1-b][1,3]benzothiazole 3. Under similar experimental conditions, compound 3 on treatment independently with arylamines/heterylamines/phenols/compounds containing active methylene group yielded corresponding 2-substituted derivatives of compound 3 (4a, 4b, 4c, 4d, 5a, 5b, 5c, 6a, 6b, 6c, 6d, 6e, and 7a, 7b, 7c, 7d, 7e). Similarly, novel heterocyclic compounds, 3-amino-4-imino-8-methoxy-2H 8a/aryl 8b–c/heteryl 8d, 8e, 8f/pyrazolo[3′,4′:4,5]pyrimido[2,1-b][1,3]benzothiazoles, were prepared by heating compound 3 independently with hydrazine hydrate/arylhydrazines/heterylhydrazines, respectively. All these newly synthesized compounds were screened for antimicrobial activity. J. Heterocyclic Chem., (2011). |
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