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Innovative cascade reaction for 2H-indazole derivative synthesis

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Abstract

In the realm of synthetic organic chemistry, by using a one-pot sequential combination of MCR, it is possible to manufacture chemical commodities (fine chemicals, agrochemicals, and pharmaceutical substances) that enhance our quality of life while generating less waste materials and increasing economic advantages. With this motivation, using a “one-pot” method with multiple components, we present a relatively simple way to make stereoselective substitute 2H-indazole analogues for this study. Firstly, functionalised 3-bromo-4-((methylthio)methyl) derivatives were produced using DMSO as both a carbon source and a solvent, in conjunction with TMSOTf as the Lewis acid promoter. These derivatives were then utilised in the synthesis of 2-H-indazole derivatives with an up to 80% yield using t-Bu3PHBF4 as the ligand and Cs2CO3 as the base, in the presence of a Pd catalyst at 100°C in an airtight tube. The phenyl ring is endowed with an electron-releasing group situated at position C-6, which efficiently synthesises several 2-H-indazol derivatives with cost-efficient and noteworthy yields by using this method. A comparative analysis of a number of halogen derivatives was also undertaken, using a variety of solvents that were classified according to their halogen group. To confirm the structures of the synthesised target compounds, spectrometric analysis (1H NMR, 13C NMR, and LCMS) was performed.

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Scheme 1
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The data underlying this study are available in the published article and its Supporting Information.

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Acknowledgements

Authors are thankful to O2h Discovery Pvt Ltd for the spectral analysis. The authors express their gratitude to Veer Narmad South Gujarat University, Surat to providing necessary lab facilities and KCG Govt. of Gujarat for Shodh fellowship.

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Authors and Affiliations

  1. Department of Chemistry, Veer Narmad South Gujarat University, Surat, Gujarat, 395007, India

    Annu Choudhary & Kishor H. Chikhalia

  2. Department of Microbiology and Biotechnology, University School of Sciences, Gujarat University Ahmedabad, Gujarat, 781014, India

    Rohit Patel & Dweipayan Goswami

Authors
  1. Annu Choudhary
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  2. Rohit Patel
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  3. Dweipayan Goswami
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  4. Kishor H. Chikhalia
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Contributions

A.C in the designing of Scheme. R.P, Dr. D. G., and Prof.K.H.Chikhalia in reviewing the manuscript and spectral analysis

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Correspondence to Kishor H. Chikhalia.

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11030_2024_10874_MOESM1_ESM.docx

Supplementary file1 (DOCX 5173 KB) Detailed experimental procedure, spectroscopic data and copies of1H NMR and13C NMR spectra for the compounds are included in supporting Information

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Choudhary, A., Patel, R., Goswami, D. et al. Innovative cascade reaction for 2H-indazole derivative synthesis. Mol Divers (2024). https://doi.org/10.1007/s11030-024-10874-0

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  • DOI: https://doi.org/10.1007/s11030-024-10874-0

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