Abstract
Cyclocondensation of monosubstituted hydrazines 2a– c with trifluoromethylenaminones 1a– c afforded 3-CF 3 and (or) 5-CF 3 pyrazoles 3– 6. Addition of N-methylhydrazine to enaminone led to 3-CF 3 pyrazole as the major product, whereas phenylhydrazine gave regiospecific formation of 5-CF 3 pyrazole. Structural assignment of regioisomers is based on 13 C NMR chemical shifts, long-range carbon–fluorine and hydrogen–fluorine coupling constants and 1 H – 1 H NOE. The pyrazole 4ac was characterized by X-ray diffraction analysis.
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