Synthesis and selected transformations of 1-(5-methyl-1-aryl-1H-1,2,3-triazol-4-yl)ethanones and 1-[4-(4-R-5-methyl-1H-1,2,3-triazol-1-yl)phenyl]ethanones

• Published in: Russian journal of general chemistry Vol. 79; no. 2; pp. 309 - 314
• Main Authors: Pokhodylo, N. T., Savka, R. D., Matiichuk, V. S., Obushak, N. D.
• Format: Journal Article
• Language: English
• Published: Dordrecht SP MAIK Nauka/Interperiodica 01.02.2009; Springer Nature
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry, Multidisciplinary; Chemistry/Food Science; Physical Sciences; Science & Technology; Quinoline; Acetylacetone; General Chemistry; Isatin; Pyrazole; CYCLOADDITION; ACETYLENES; INHIBITION; DERIVATIVES; 1,2,3-TRIAZOLE
• ISSN: 1070-3632; 1608-3350
• DOI: 10.1134/S1070363209020248

By cycloaddition of arylazides to acetylacetone are obtained derivatives of 1,2,3-triazole. In the reaction of 1-[5-methyl-1-(R-phenyl)-1 H -1,2,3-triazol-4-yl] ethanones ( IIa–IIe ) and 1-[4-(4-R-5-methyl-1 H -1,2,3-triazol-1-yl)phenyl] ethanones ( VIIa-VIIe ) with isatin are obtained 2-[1-(R-phenyl)-5-methyl-1 H -1,2,3-triazol-4-yl]-4-quinolinecarboxylic acids ( IIIa–IIIe ) and 2-[4-(4-R-5-methyl-1 H -1,2,3-triazol-1-yl)phenyl] -4-quinolinecarboxylic acids ( IXa, IXb ), respectively. We found that 1-[5-methyl-1-(R-phenyl)-1 H -1,2,3-triazol-4-yl] ethanones ( IIa–IIe ) readily transform into [5-methyl-1-(R-phenyl)-1 H -1,2,3-triazol-4-yl] acetic acids ( IVa–IVc ) by the method of Wilgerodt-Kindler. The (5-methyl-1-phenyl-1 H -1,2,3-triazol-4-yl)acetic acid reacts with 5-phenyl-4-amino-4 H -1,2,4-triazol-3-thiol affording 6-[(5-methyl-1-phenyl-1 H -1,2,3-triazol-4-yl) methyl]-3-phenyl[1,2,4] triazolo[3,4- b ] [1,3,4] thiadiazole ( VI ).