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Synthesis of fully substituted pyrazoles via regioselective 1,3-dipolar cycloaddition reaction

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Abstract

A regioselective and convenient method for the synthesis of fully substituted pyrazole derivatives was developed from the 1,3-dipolar cycloaddition reaction of nitrile imine generated in situ from hydrazonoyl chloride and Et3N with 1,4-benzothiazin-3(4H)-one. The structure of the target molecule 3d was confirmed by X-ray diffraction.

Graphical Abstract

An efficient synthesis of a series of 1H-pyrazole-4-carboxylate is reported. A multicomponent reaction was designed using 2-aminothiophenol, dialkyl acetylenedicarboxylate, and hydrazonoyl chloride in the presence of Et3N in EtOH at room temperature. The structure of the target molecules was confirmed by X-ray diffraction.

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Acknowledgements

We gratefully acknowledge the support of this work by the Tarbiat Modares University Research Council.

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Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran

    Abdolali Alizadeh & Leila Moafi

  2. Department of Chemistry, Zhejiang University, Hangzhou, 310027, People’s Republic of China

    Long-Guan Zhu

Authors
  1. Abdolali Alizadeh
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  2. Leila Moafi
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  3. Long-Guan Zhu
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Correspondence to Abdolali Alizadeh.

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Alizadeh, A., Moafi, L. & Zhu, LG. Synthesis of fully substituted pyrazoles via regioselective 1,3-dipolar cycloaddition reaction. J IRAN CHEM SOC 15, 1255–1259 (2018). https://doi.org/10.1007/s13738-018-1323-1

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  • DOI: https://doi.org/10.1007/s13738-018-1323-1

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