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Unraveling the access to the regioselective synthesis of highly functionalized pyranopyrazoles using an ionic liquid catalyst

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Abstract

An efficient and green strategy for the regioselective synthesis of highly functionalized pyranopyrazole via one-pot condensation of 3-methyl-1-phenyl-5-pyrazolone or EAA and hydrazine hydrate, substituted aromatic aldehydes with NMSM [(E)-N-Methyl-1-(methylthio)-2-nitro-ethenamine] in the existence of IL [(EMIM)Ac] as catalyst with solvent-free condition (SFC) is described. This domino protocol produces biologically substantial heterocycles through Knoevenagel condensation proceeded by Michael addition and O-cyclization with an eradication of methanethiol group, which create the one stereo-center and creation of “C–C, C–N, C–O, C=C, C=N, bonds.” The final product is produced by exceptionally easy filtering after the reaction mass was triturated with ethanol. The strategy's noteworthy features include the use of biodegradable IL catalyst, excellent to exceptional yield with rapid reaction times, applicability to a wide range of substrate, clear reaction profile, and straightforward workup process.

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  1. aIsolated yield

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Acknowledgements

SAIF-PU, Panjab University, Chandigarh, provided the spectrum data, such as 1H & 13C NMR, to the authors, and they would like to express their gratitude for their assistance in this study. This research work would not have been possible without the general facilities provided by Deogiri College, Aurangabad.

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Authors and Affiliations

  1. Department of Chemistry, SAJVPM’S, Smt. S. K. Gandhi Arts, Amolak Science and P. H. Gandhi Commerce College, Kada, 414202, Maharashtra, India

    Ashishkumar P. Katariya

  2. Department of Chemistry, Institute of Science, Nagpur, 440001, Maharashtra, India

    Prakash D. Shirsath

  3. Department of Chemistry, Indrashil University, Kadi, Rajpur, India

    Hanuman Narode

  4. Department of Chemistry, New Arts, Commerce and Science College, Ahmednagar, 414 001, Maharashtra, India

    Pravinkumar B. Gaikwad

  5. Department of Chemistry, Shri Datta Arts & Commerce College, Tamsa Rd, Hadgaon, 431712, Maharashtra, India

    Gajanan G. Kadam

  6. Department of Chemistry, Muktanand College, Gangapur, 431109, Maharashtra, India

    Maya V. Katariya

  7. Department of Chemistry, Deogiri College, Aurangabad, 431005, Maharashtra, India

    Ashishkumar P. Katariya & Satish U. Deshmukh

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  1. Ashishkumar P. Katariya
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11030_2022_10572_MOESM1_ESM.docx

Supplementary file1 (DOCX 3321 KB) The IR, 1H, 13C NMR, and HRMS spectra of new and a few previously known pyranopyrazole compounds are included in a supporting information also consist of a table shows synthesized compound’s yield and melting point

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Katariya, A.P., Shirsath, P.D., Narode, H. et al. Unraveling the access to the regioselective synthesis of highly functionalized pyranopyrazoles using an ionic liquid catalyst. Mol Divers 27, 2633–2649 (2023). https://doi.org/10.1007/s11030-022-10572-9

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