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An efficient and facile synthesis of divergent C-3/C-5 bis-functionalized 2-oxindoles from 5-formyl-Morita-Baylis-Hillman adducts of oxindole

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Abstract

An efficient and facile synthesis of divergent C-3/C-5 bis-functionalized 2-oxindole derivatives has been achieved from 3,5-bis-Morita-Baylis-Hillman (MBH) adducts of oxindole via nucleophilic substitution reaction for the first time. Wider scope of substrate and rate acceleration has been observed in second MBH reaction under typical reaction condition. The synthetic usefulness of bi-functionalized bis-allyl derivative has been demonstrated by the synthesis of potent bis-pyrazole via [3 + 2]-annulation strategy.

An efficient and facile synthesis of divergent C-3/C-5 bis-functionalized 2-oxindoles has been achieved from 3,5-bis-Morita-Baylis-Hillman (MBH) adducts. A wider substrate scope/rate acceleration has been noted under a typical reaction condition and also the synthetic usefulness of bis-allyl derivatives has been demonstrated by the synthesis of potent bis-pyrazole via [3+2]- annulation strategy.

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Acknowledgements

KS thanks Thiagarajar College, Madurai; KAP thanks Kamaraj College, Tuticorin; and PS thank Tamilnadu Open University, Chennai, for providing lab facilities. RVLV thanks director of NIIST for providing infrastructure facilities. Thanks are due to Mrs. Viji and Mrs. Saumini Mathew for providing Mass and NMR spectra.

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Authors and Affiliations

  1. Department of Chemistry, Thiagarajar College, Madurai, 625 009, Tamil Nadu, India

    KODIRAJAN SELVAKUMAR

  2. Department of Chemistry, Kamaraj College, Tuticorin, 628 003, Tamil Nadu, India

    KANDAPALAM ARUN PRASATH LINGAM

  3. Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram, 695 019, Kerala, India

    RAMA VARMA LUXMI VARMA

  4. Department of Chemistry, School of Science, Tamilnadu Open University, Saidapet, Chennai, 600 015, Tamil Nadu, India

    POOVAN SHANMUGAVELAN

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  1. KODIRAJAN SELVAKUMAR
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  2. KANDAPALAM ARUN PRASATH LINGAM
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  3. RAMA VARMA LUXMI VARMA
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  4. POOVAN SHANMUGAVELAN
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Correspondence to KODIRAJAN SELVAKUMAR or POOVAN SHANMUGAVELAN.

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Supplementary Information

The electronic supplementary information consists of the general procedure for the synthesis of target molecules and their analytical data/spectral proof in detail. Supplementary Information is available at www.ias.ac.in/chemsci.

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SELVAKUMAR, K., PRASATH LINGAM, K.A., LUXMI VARMA, R.V. et al. An efficient and facile synthesis of divergent C-3/C-5 bis-functionalized 2-oxindoles from 5-formyl-Morita-Baylis-Hillman adducts of oxindole. J Chem Sci 127, 1417–1426 (2015). https://doi.org/10.1007/s12039-015-0913-z

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