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An efficient domino Knoevenagel/hetero-Diels–Alder route to some novel thiochromenoquinoline-fused polyheterocycles

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Abstract

The 2-alkenylthiopyranoquinoline-3-carbaldehyde derived from 2-mercaptoquinoline-3-carbaldehyde and citral underwent smooth domino Knoevenagel/hetero-Diels–Alder reaction with heterocyclic mono- or diketones in tetrabutylammonium hydrogensulfate under solvent-free conditions and afforded a new class of thiochromenoquinoline-fused heterocycles in good yields. The reaction is highly diasteroselective and can be applied to analogues of carbocyclic diketones as well. The stereochemistry of the products was confirmed by single-crystal X-ray diffraction and 2D NMR NOESY data.

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Acknowledgments

The authors thank the Head of the Department of Chemistry, S. P. University, for providing the necessary research facilities, and the UGC (University Grants Commission), New Delhi, for financial support under the UGC Scheme of Major Research (Project Number 39-822/2010 (SR) dated 11.01.2011).

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Authors and Affiliations

  1. Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, 388120, Anand, Gujarat, India

    Narsidas J. Parmar, Balvantsingh M. Labana & Hitesh A. Barad

  2. Department of Physics, University of Jammu, Jammu-Tawi, 180006, India

    Rajni Kant & Vivek K. Gupta

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  1. Narsidas J. Parmar
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  2. Balvantsingh M. Labana
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  3. Hitesh A. Barad
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Correspondence to Narsidas J. Parmar.

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Parmar, N.J., Labana, B.M., Barad, H.A. et al. An efficient domino Knoevenagel/hetero-Diels–Alder route to some novel thiochromenoquinoline-fused polyheterocycles. Monatsh Chem 145, 1179–1189 (2014). https://doi.org/10.1007/s00706-014-1187-8

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