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

Literature Information

Publication Date 2017-12-04
DOI 10.1039/C7OB02523H
Impact Factor 3.876
Authors

Amol D. Sonawane, Dinesh R. Garud, Taro Udagawa, Mamoru Koketsu


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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. Furthermore, by employing various palladium-catalyzed Sonogashira, Suzuki, and Heck reactions, the structural diversification of the resulting halide derivatives, which can act as the important intermediates for building other valuable compounds, was achieved. 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. Furthermore, the reaction process was well elucidated by density functional theory calculations.

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