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Synthesis of thieno[2,3–b]quinoline and selenopheno[2,3–b]quinoline derivatives via iodocyclization reaction and DFT mechanistic study

Abstract

In this letter, we report the regioselective iodocyclization reaction of 3-alkynyl-2-(methylthio)quinolines and 3-alkynyl-2-(methylseleno)quinolines for the synthesis of thieno[2,3–b]quinoline and selenopheno[2,3–b]quinoline derivatives. Further, the resulting halides derivatives were allowed for structural diversification by employing various palladium-catalyzed Sonogashira, Suzuki, and Heck reactions, which can act as the important intermediates for building other valuable compounds. All compounds were fully characterized by the FT-IR, mass, 1H NMR, and 13C NMR spectral data. Finally, the structure of the thieno[2,3–b]quinoline derivative was confirmed by X–ray crystallography. This methodology provided a novel pathway to access quinoline fused heterocycles via iodocyclization reaction. Further, the reaction process was well elucidated by density functional theory calculations.

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Publication details

The article was received on 12 Oct 2017, accepted on 04 Dec 2017 and first published on 04 Dec 2017


Article type: Paper
DOI: 10.1039/C7OB02523H
Citation: Org. Biomol. Chem., 2017, Accepted Manuscript
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    Synthesis of thieno[2,3–b]quinoline and selenopheno[2,3–b]quinoline derivatives via iodocyclization reaction and DFT mechanistic study

    A. D. Sonawane, D. R. Garud, T. Udagawa and M. Koketsu, Org. Biomol. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7OB02523H

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