W. Peng, Shizheng Zhu
Jun 9, 2003
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Influential Citations
57
Citations
Journal
Tetrahedron
Abstract
Abstract A series of 5-fluoroalkylated 1 H -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 β,β-difluoro-β-triazolyl alcohol derivatives, which were lactonized with catalytic amount of p -toluenesulfonic acid in toluene at 80–90°C to give a series of novel bicyclic gem -difluorinated 1 H -pyrano[3,4- d ][1,2,3]-triazol-4-one compounds in good yield.