Paper
A New Approach to Ethyl 1-Aroyl/Aroylmethyl-5-methyl-3-methylthiopyrazole-4-carboxylates: High Regioselectivity in Alkylation and Acylation Reactions between N-1 and N-2 of a Pyrazole Derivative
Published Sep 1, 2005 · L. Wen, Guilong Zhao, Ming Li
Chinese Chemical Letters
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Abstract
Two series, totalizing twelve, of new compounds, ethyl 1-aroyllaroylmethyl-5-methyl-3-methylthiopyrazole-4-carboxylates 5/6, have been synthesized via highly regioselective acylation and alkylation of ethyl 3-methyl-5-methylthio-1H-pyrazole-4-carboxylate 2a with aroyl chloride 3 and alpha-tosyloxysubstitutedacetophenones 4. Unexpected structures of the product have been unambiguously determined by both X-ray crystallographic analysis and 2D NMR.
This study demonstrates a new method for synthesizing ethyl 1-aroyl/aroylmethyl-5-methyl-3-methylthiopyrazole-4-carboxylates with high regioselectivity, providing potential applications in pharmaceuticals and nutraceuticals.
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