Affiliation:
1. Department of Chemistry, University of Johannesburg, PO Box 524, Auckland Park, 2006, South Africa
2. Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, USA
Abstract
A high-yield, solvent-free approach to the synthesis of 1,3,5-trisubstituted pyrazoles is reported. Four compounds, (3,5-di-tert-butyl-1H-pyrazole, (2-(3,5-dimethyl-1H-pyrazol-1-yl)ethanol, 2-(3,5-di-tert-butyl-1H-pyrazol-1-yl)ethanol, 2-(3,5-diphenyl-1H-pyrazol-1-yl)ethanol were readily prepared by solvent-free condensation of the appropriate dike-tone and the respective hydrazine. The crystal structures of the three pyrazolyl-ethanols are typical of N-substituted pyrazoles. All three pyrazolyl compounds show interesting inter-molecular hydrogen bonding. For the 3,5-dimethyl compound the molecules form discrete hydrogen bonded dimers within a unit cell, while for the others the hydrogen bonding is in a head-to-tail arrangement resulting in the formation of chains.
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