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Synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] and spiro[indoline-3,4′-pyrano[2,3-c]chromene] derivatives using silica-bonded ionic liquids as a recyclable catalyst in aqueous medium

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Abstract

Silica-bonded ionic liquids is employed as a recyclable catalyst for the synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazoles] via one-pot condensation reaction of isatin, activated methylene reagents, and 3-methyl-l-phenyl-5-pyrazolone in refluxing aqueous medium in good to high yields. Also, these silica-bonded ionic liquids were used as catalysts for the synthesis of spiro[indoline-3,4′-pyrano[2,3-c]chromene derivatives in refluxing aqueous medium in high yields. Catalyst could be recycled for several times without any additional treatment.

Graphical Abstract

Silica-bonded ionic liquids is employed as a recyclable catalyst for the synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazoles] and spiro[indoline-3,4′-pyrano[2,3-c]chromene via one-pot condensation reaction of isatin, activated methylene reagents, and 3-methyl-l-phenyl-5-pyrazolone or 4-hydroxy coumarin respectively in refluxing aqueous medium in good to high yields.

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Acknowledgments

We are thankful to Persian Gulf University Research Council for partial support of this work. Also, we are thankful to the School of Chemistry, Manchester University for running NMRs.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr, 75169, Iran

    Khodabakhsh Niknam, Abolhassan Piran & Zahra Karimi

Authors
  1. Khodabakhsh Niknam
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  2. Abolhassan Piran
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  3. Zahra Karimi
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Correspondence to Khodabakhsh Niknam.

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Niknam, K., Piran, A. & Karimi, Z. Synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] and spiro[indoline-3,4′-pyrano[2,3-c]chromene] derivatives using silica-bonded ionic liquids as a recyclable catalyst in aqueous medium. J IRAN CHEM SOC 13, 859–871 (2016). https://doi.org/10.1007/s13738-015-0801-y

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