Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 8, Pages 5370-5378Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00078
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Funding
- Council of Scientific and Industrial Research (CSIR). SERB
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An efficient, metal-free approach to access pyrazolo-[1,5-c]quinazolines with 3-ylideneoxindoles and tosyldiazomethane (TsDAM) under mild aqueous reaction conditions has been developed and the solvent involvement in the present reaction has also been explored for the first time. This greener approach involves 1,3-dipolar cycloaddition, regioselective ring expansion, followed by the elimination of tosyl group with aqueous base in a single operation, and the product can be isolated in high purity without column chromatographic separation. The method is also compatible with a large variety of functional groups, providing good to excellent yields in water, thus resulting in a decrease of environmental impact in the pharmaceutical industry.
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