Synthesis of Novel Pyrazoles via [2+3]-Dipolar Cycloaddition Using Alkyne Surrogates.
The syntheses of an important class of hitherto unreported novel pyrazoles are described. The regioselective synthesis of 1,3,4,5-tetrasubstituted pyrazoles was achieved by the Huisgen cyclization of nitrile imines with a trisubstituted bromoalkene. The substituted bromoalkene functions as an alkyne synthon which was used to construct 5,5-disubstituted bromopyrazoline intermediates that undergo aromatization to the analogous pyrazoles through the loss of HBr. The cycloaddition regioselectivity was confirmed through single X-ray crystal data of one of the pyrazoles.
Dadiboyena
Sureshbabu
S
Department of Chemistry & Biochemistry, College of Science, Engineering and Technology, Jackson State University, Jackson, Mississippi 39217 USA.
Valente
Edward J
EJ
Hamme
Ashton T
AT