Abstract
Pyrazinamide (I) was derived to its 1- or 4-oxide by treatment with hydrogen peroxide and treated with phosphoryl chloride to form chloropyrazinecarbonitrile. Its hydrolysis with hydrochloric acid afforded 5- and 6-chloropyrazinamide (VII and VIII). Thioethers were prepared by application of thiophenol, p-thiocresol, o-mercaptobenzoic acid, p-aminothiophenol, p-nitrothiophenol, and p-acetamidobenzenesulfonyl chloride to (III) and (VII), and various 5-substituted Pyrazinamide derivatives were prepared by oxidation of these obtained thioethers with hydrogen peroxide. Antituberculosis action of these compounds was tested and (IX) and (XI) were found to have excellent action against tubercle bacilli.
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