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Issue 11, 2019
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Tetrahydroquinolines by the multicomponent Povarov reaction in water: calix[n]arene-catalysed cascade process and mechanistic insights

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Abstract

The catalyst p-sulfonic acid calix[4]arene was effectively used in the three-component Povarov reaction between aromatic anilines and two equivalents of 2,3-dihydrofuran to obtain furano[3,2-c]-1,2,3,4-tetrahydroquinolines. These reactions proceeded efficiently using water as a green solvent and nontoxic catalysts that could be efficiently reused; the reactions were metal-free and used only inexpensive and easily available compounds. Together with a simple workup procedure, these advantages make this protocol a very efficient and green alternative to the traditional methods for constructing tetrahydroquinoline structures, through the formation of two new C–C bonds and one C–N bond. Isotopic labelling experiments revealed the mechanism for the Povarov reactions, showing that the reaction proceeds through a sequence of steps via ionic intermediates, and the proposed reaction mechanism was validated.

Graphical abstract: Tetrahydroquinolines by the multicomponent Povarov reaction in water: calix[n]arene-catalysed cascade process and mechanistic insights

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Publication details

The article was received on 23 Nov 2018, accepted on 30 Jan 2019 and first published on 30 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB02928H
Citation: Org. Biomol. Chem., 2019,17, 2913-2922

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    Tetrahydroquinolines by the multicomponent Povarov reaction in water: calix[n]arene-catalysed cascade process and mechanistic insights

    T. R. M. Rezende, J. O. S. Varejão, A. L. L. D. A. Sousa, S. M. B. Castañeda and S. A. Fernandes, Org. Biomol. Chem., 2019, 17, 2913
    DOI: 10.1039/C8OB02928H

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