Base Induced Cyclocondensation of Arylhydrazines with α,β-Bis(methylthio)-α,β-unsaturated-1,4-diketones: A Novel Approach for the Synthesis of 1,3-Di(hetaryl/aryl)-4-methylthio-5-acyl-pyrazoles

We herein report the reaction between α-oxodithioesters and methyl ketones in the presence of sodium hydride and methyl iodide in DMF for the synthesis of symmetrical α,β-bis(methylthio)-α,β-unsaturated-1,4-diketones, which are novel key compounds. We explored potential application of these intermediates by reacting with arylhydrazines in the presence of potassium hydroxide in isopropyl alcohol at 75 °C, which afforded 1,3-di(hetaryl/aryl)-4-methylthio-5-acyl-pyrazoles in high yields and short reaction times. Wide substrate scope, development of novel key intermediates and pyrazoles, are the advantages of this protocol

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Publication Details

Journal
Synthesis
Published
2026-08-18
DOI
https://doi.org/10.1055/a-2936-1489
Primary Topic
Synthesis of heterocyclic compounds
Type
article
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article

Base Induced Cyclocondensation of Arylhydrazines with α,β-Bis(methylthio)-α,β-unsaturated-1,4-diketones: A Novel Approach for the Synthesis of 1,3-Di(hetaryl/aryl)-4-methylthio-5-acyl-pyrazoles

Varadaraj Bhat G, Kempegowda Mantelingu, Nagarakere C. Sandhya, Toreshettahally R. Swaroop et al.
Synthesis
Synthesis of heterocyclic compounds
article

Base Induced Cyclocondensation of Arylhydrazines with α,β-Bis(methylthio)-α,β-unsaturated-1,4-diketones: A Novel Approach for the Synthesis of 1,3-Di(hetaryl/aryl)-4-methylthio-5-acyl-pyrazoles

Varadaraj Bhat G, Kempegowda Mantelingu, Nagarakere C. Sandhya, Toreshettahally R. Swaroop, Siddanakatte L. Prapullachandra, Aditi Nayak
article en

Abstract

We herein report the reaction between α-oxodithioesters and methyl ketones in the presence of sodium hydride and methyl iodide in DMF for the synthesis of symmetrical α,β-bis(methylthio)-α,β-unsaturated-1,4-diketones, which are novel key compounds. We explored potential application of these intermediates by reacting with arylhydrazines in the presence of potassium hydroxide in isopropyl alcohol at 75 °C, which afforded 1,3-di(hetaryl/aryl)-4-methylthio-5-acyl-pyrazoles in high yields and short reaction times. Wide substrate scope, development of novel key intermediates and pyrazoles, are the advantages of this protocol

Synthesis
Manipal Academy of Higher Education (IN), University of Mysore (IN), G.S. Science, Arts And Commerce College (IN)
Clean water and sanitation
Openalex Percentile: Top 18%
Synthesis of heterocyclic compounds
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