@Article{IPB-403, author = {Zanatta, N. and Mittersteiner, M. and Aquino, E. C. and Budragchaa, T. and Wessjohann, L. A. and Bonacorso, H. G. and Martins, M. A. P.}, title = {{Synthesis of methylene-bridged trifluoromethyl azoles using 5-(1,2,3-Triazol-1-yl)enones}}, year = {2022}, pages = {439-450}, journal = {Synthesis}, doi = {10.1055/s-0040-1719837}, url = {https://doi.org/10.1055/s-0040-1719837}, volume = {54}, abstract = {A protocol for synthesizing triazole-containing pyrazolines and pyrazoles selectively using trifluoromethylated 5-(1,2,3-triazol-1-yl)enones as starting materials, is reported. The selectivity of the reaction was controlled by the nature of the hydrazine or derivative used: free hydrazines furnished the 1,5-regiosiomer exclusively in yields up to 98%, whereas protected hydrazines provided the 1,3-regioisomer in yields up to 77%. To demonstrate the synthetic versatility of the triazole-based enone, reactions with other unsymmetrical dinucleophiles (hydroxylamine hydrochloride and S-methyl isothiourea sulfates) allowed the selective preparation of triazole-containing isoxazoline and pyrimidine rings.} }