Efficient approach to androstene-fused arylpyrazolines as potent antiproliferative agents. Experimental and theoretical studies of substituent effects on BF(3)-catalyzed intramolecular [3 + 2] cycloadditions of olefinic phenylhydrazones.

Abstract

Highly diastereoselective Lewis acid induced intramolecular 1,3-dipolar cycloadditions of alkenyl phenylhydrazones (containing various substituents on the aromatic ring) obtained from a d-secopregnene aldehyde were carried out under fairly mild conditions to furnish androst-5-ene-fused arylpyrazolines in good to excellent yields. The ability of… (More)
DOI: 10.1021/ja808636e

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@article{Frank2009EfficientAT, title={Efficient approach to androstene-fused arylpyrazolines as potent antiproliferative agents. Experimental and theoretical studies of substituent effects on BF(3)-catalyzed intramolecular [3 + 2] cycloadditions of olefinic phenylhydrazones.}, author={{\'E}va Frank and Zolt{\'a}n Mucsi and Istvan Zupko and Borb{\'a}la R{\'e}thy and George Falkay and Gyula Schneider and J{\'a}nos W{\"{o}lfling}, journal={Journal of the American Chemical Society}, year={2009}, volume={131 11}, pages={3894-904} }