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Syntheses of 1-(4-methylsulfonylphenyl)-5-aryl-1,2,3-triazoles and -(4-aminosulfonylphenyl)-5-aryl-1,2,3-triazoles

✍ Scribed by F. Johari Daha; H. Matloubi; S. A. Tabatabi; B. Shafii; A. Shafiee

Publisher: Journal of Heterocyclic Chemistry
Year: 2005
Tongue: English
Weight: 60 KB
Volume: 42
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570420106

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✦ Synopsis

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.

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