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A one-pot three-component reaction involving 2-aminochromone in aqueous micellar medium: a green synthesis of hexahydrochromeno[2,3-\(b\)]quinolinedione

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Abstract

An efficient and green synthesis of hitherto unreported 11-(chromen-3-yl)-8,8-dimethyl-8,9-dihydro-6\(\textit{H}\)-chromeno[2,3-\(b\)]quinoline-10,12(7\(\textit{H}\),11\(\textit{H}\))-dione has been accomplished by a three-component reaction involving 2-aminochromone, chromone-3-carbaldehyde, and 5,5-dimethyl-1,3-cyclohexanedione (dimedone) in 0.5 M aqueous SDS solution. The mechanism of the reaction has been studied by isolating the reaction intermediate. This methodology features eco-friendly reaction conditions, a simple working procedure, high atom-economy and high efficiency in product formation.

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Acknowledgments

We gratefully acknowledge CSIR, New Delhi [Project no. 02(0029)/11/EMR-II] for financial assistance; DST-FIST for instrumental help at RKMVC College; IICB, Jadavpur and Kalyani University for spectral analysis and finally the college authority for providing research facilities. J. G. thanks CSIR for Senior Research Fellowship.

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Authors and Affiliations

  1. Department of Chemistry, R. K. Mission Vivekananda Centenary College, Rahara, Kolkata, 700118, West Bengal, India

    Jaydip Ghosh, Pritam Biswas & Chandrakanta Bandyopadhyay

  2. Department of Chemistry, The University of Reading, P. O. Box 224, Whiteknights, Reading, RG6 6AD, UK

    Michael G. B. Drew

Authors
  1. Jaydip Ghosh
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  2. Pritam Biswas
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  3. Michael G. B. Drew
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  4. Chandrakanta Bandyopadhyay
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Correspondence to Chandrakanta Bandyopadhyay.

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11030_2015_9573_MOESM1_ESM.doc

\(^{1}\)H NMR, \(^{13}\)C NMR and Mass spectral data for hexahydrochromeno[2,3-\(b\)]quinolinediones 7a–7k, 13a and 11a,11b are available. Crystallographic data of 7a (CCDC 1008775) and 7i(CCDC 1008776) have been deposited at the Cambridge Crystallographic Database Centre and are available on request (http://www.ccdc.cam.ac.uk)

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Ghosh, J., Biswas, P., Drew, M.G.B. et al. A one-pot three-component reaction involving 2-aminochromone in aqueous micellar medium: a green synthesis of hexahydrochromeno[2,3-\(b\)]quinolinedione. Mol Divers 19, 541–549 (2015). https://doi.org/10.1007/s11030-015-9573-7

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