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Metal Acetylacetonates Covalently Anchored onto Amine Functionalized Silica/Starch Composite for the One-Pot Thioetherification and Synthesis of 2H-Indazoles

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Abstract

This paper reports a series of novel metal acetylacetonates covalently anchored onto amine functionalized silica/starch composite, prepared by the Schiff condensation of metal acetylacetonates [Co(acac)2, Cu(acac)2, Pd(acac)2, Ru(acac)3, Mn(acac)3, Co(acac)3] with organically modified 3-aminopropyl silica/starch composite. Different metal acetylacetonates have been chosen with a view to select the most active heterogeneous catalyst. Among various catalysts, covalently anchored Cu(acac)2 onto amine functionalized silica/starch composite [ASS-Cu(acac)2] was found to be the most active and recyclable catalyst for the one-pot thioetherification and one-pot three component synthesis of 2H-indazoles via consecutive C–N and N–N bond formations. All the catalysts were characterized by FTIR, TGA and AAS analysis and the most active catalyst, [ASS-Cu(acac)2] was further characterized by SEM and TEM. The catalyst could be recovered by simple filtration and reused with almost consistent activity for four consecutive runs.

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Acknowledgements

We thank the Head, Regional Sophisticated Instrumentation Centre, Nagpur University, Nagpur for AAS analysis; Head, SAIF, Punjab University Chandigarh for FT-IR and SEM and Head, SAIF, IIT Bombay for TEM studies, Director IIIM Jammu for CHNS elemental analysis. We gratefully acknowledge Department of Science and Technology, Government of India for NMR spectrometer (Bruker Avance III, 400 MHz) under PURSE program to the University of Jammu, Department of Chemistry, University of Jammu for spectral and TGA analysis. We also thank UGC, New Delhi for financial support (SAP, DRS I and Major research Project, F-41-281/2012 (SR).

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  1. Department of Chemistry, University of Jammu, Jammu, 180 006, India

    Ravinderpal Kour Sodhi, Avtar Changotra & Satya Paul

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  1. Ravinderpal Kour Sodhi
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  2. Avtar Changotra
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  3. Satya Paul
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Correspondence to Satya Paul.

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Sodhi, R.K., Changotra, A. & Paul, S. Metal Acetylacetonates Covalently Anchored onto Amine Functionalized Silica/Starch Composite for the One-Pot Thioetherification and Synthesis of 2H-Indazoles. Catal Lett 144, 1819–1831 (2014). https://doi.org/10.1007/s10562-014-1345-y

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