THE PREPARATION OF 3-(2-PHENYLETHENYL)-1H-PYRAZOLES FROM DILITHIATED (3E)-4-PHENYL-3-BUTEN-2-ONE HYDRAZONES

Abstract

The phenyl-, carbomethoxy-, and carboethoxy-hydrazones of (3E)-4-phenyl-3-buten-2-one [benzalacetone] were treated with excess lithium diisopropylamide, and the resulting 1,4-dianions were condensed with several aromatic esters, followed by acid cyclization of C-acylated intermediates, to afford substituted 3-(2-phenylethenyl)-1H-pyrazoles [3-styryl-pyrazoles].

ACKNOWLEDGMENTS

We thank the National Science Foundation's Research in Undergraduate Institutions through grant # 9708014, along with the Donors of the Petroleum Research Fund, administered by the American Chemical Society, for support. The acquisition of the 300 MHz NMR spectrometer was made possible through the National Science Foundation's Division of Undergraduate Education grant DUE # 9750721.