Condensation of 4-methylsulfonylaniline with aryl aldehyde in ethanol-tetrahydrofuran afforded the imino compound 3. 1,3-Cycloaddtion of diazomethane with compound 3 followed by oxidazation of the triazoline 4 with potassium permanganate gave 1-(4-methylsulfonylphenyl)-5-aryl-1,2,3-triazoles 5. Similarly, condensation of 4-(N,N-dibenzylaminosulfonyl)aniline with aryl aldehyde followed by l,3-cycloaddition of diazomethane with the imino compound 11 and the subsequent oxidation of triazoline 12 with potassium permanganate yielded the triazole 13. Debenzylation of compound 13 with sulfuric acid gave the desired compound 1-(4-aminosulfonylphenyl)-5-aryl-1,2,3-triazoles 14.

Triazole derivatives Triazole derivatives R 0280Syntheses of 1-(4-Methylsulfonylphenyl)-5-aryl-1,2,3-triazoles and 1-(4-Aminosulfonylphenyl)-5-aryl-1,2,3-triazoles. -Biaryltriazoles (VI) and (XII) are synthesized as possible COX-2 inhibitors. Some reaction steps according to literature methods are slightly modified to start the reaction or to improve the reaction yields. For example, potassium permanganate oxidation of (V) in an acetone solution affords the desired product (VI) only in low yield. However, this compound can be obtained in moderate to good yield using potassium permanganate in a two-phase system in the presence of a phase-transfer catalyst. Because the cycloaddition of diazomethane (IV) with sulfonamide-group-bearing imino compound fails, the synthesis of triazole (XII) involves the protection of the amino group as dibenzylamine, cf. (IX). -(DAHA, F. J.; MATLOUBI, H.; TABATABI, S. A.; SHAFII, B.; SHAFIEE*, A.; J. Heterocycl.