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An efficient and rapid synthesis of 3-hydroxy-3-alkyl-2-oxindoles via Zn-mediated barbier-type reaction under aqueous conditions

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Abstract

 A robust and rapid synthesis of 3-hydroxy-3-alkyl-2-oxindoles from isatins is described. This method introduces an ecofriendly, un-activated Zn dust, solid \(\hbox {NH}_{4}\hbox {Cl}\) and substrates under aqueous conditions, which has produced the product in moderate to good yields. Without using column chromatography, majority of the compounds were isolated in analytically pure form. The progress of the reaction could be visualized by naked eye.

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SYNOPSIS A robust and rapid synthesis of 3-hydroxy-3-alkyl-2-oxindoles from isatins is described. This method introduces an ecofriendly method using un-activated Zn dust, solid \(\hbox {NH}_{4}\hbox {Cl}\) and substrates under aqueous conditions, which has produced the products in moderate to good yields.

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Fig. 1
Scheme 1
Scheme 2

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Acknowledgements

L. R. C thanks DST-SERB (SB/EMEQ-304/2014) for funding and M. S. R thanks UGC for Non-NET fellowship. Authors are grateful to Prof. S. A Bari Hon’ble Vice-Chancellor, CUG for his kind support and encouragement.

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Authors and Affiliations

  1. Centre for Applied Chemistry, Central University of Gujarat, Gandhinagar, Gujarat, 382 030, India

    L Raju Chowhan & Nandigama Satish Kumar

  2. School of Chemical Sciences, Central University of Gujarat, Gandhinagar, Gujarat, 382 030, India

    Marri Sameer Reddy

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  1. L Raju Chowhan
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Correspondence to L Raju Chowhan.

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Chowhan, L.R., Reddy, M.S. & Kumar, N.S. An efficient and rapid synthesis of 3-hydroxy-3-alkyl-2-oxindoles via Zn-mediated barbier-type reaction under aqueous conditions. J Chem Sci 129, 1205–1209 (2017). https://doi.org/10.1007/s12039-017-1329-8

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