Efficient synthesis of 5-fluoroalkylated 1H-1,2,3-triazoles and application of the bromodifluoromethylated triazole to the synthesis of novel bicyclic gem-difluorinated 1H-pyrano[3,4-d][1,2,3]-triazol-4-one compounds
β Scribed by Weimin Peng; Shizheng Zhu
- Book ID
- 104205321
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 259 KB
- Volume
- 59
- Category
- Article
- ISSN
- 0040-4020
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β¦ Synopsis
A series of 5-fluoroalkylated 1H-1,2,3-triazoles were synthesized in good yield by the regiospecific 1,3-dipolar cycloaddition reaction of (Z)-ethyl 3-fluoroalkyl-3-pyrrolidino-acrylates with aryl or benzyl azides. In the cases of benzyl azides, addition of Na 2 CO 3 was crucial for a high yield of the triazoles. Tetrakis(dimethylamino)ethylene (TDAE) promoted reaction of bromodifluoro-methylated triazole with aldehydes affording a new class of b,b-difluoro-b-triazolyl alcohol derivatives, which were lactonized with catalytic amount of p-toluenesulfonic acid in toluene at 80 -908C to give a series of novel bicyclic gem-difluorinated 1H-pyrano [3,4-d][1,2,3]-triazol-4-one compounds in good yield.
π SIMILAR VOLUMES
## By means of regioselective S-alkylation of 1H-1,2,4-triazole-3-thiol (1), a series of S-substituted derivatives 2a-j were synthesized. In certain conditions, the reaction of 2 with arylsulfochlorides, arylisocyanates, and quaternary ammonium salts of azines corresponding compounds were obtained