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Issue 1, 2009
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Synthesis of highly substituted 2-perfluoroalkyl quinolines by electrophilic iodocyclization of perfluoroalkyl propargyl imines/amines

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Abstract

A series of highly substituted 2-perfluoroalkyl-3-iodoquinolines are prepared by two different methods in good to excellent yields under mild reaction conditions. The first method involves iodocyclization of perfluoroalkyl propargyl imines with I2-CAN. The second method involves iodocyclization of perfluoroalkyl propargyl amines using I2 and ICl. The perfluoroalkyl propargyl amines are prepared in excellent yields viaSonogashira coupling of easily accessible imidoyl iodides with alkynes followed by reduction with NaBH3CN. The scope of this methodology is extended by using the resulting 2-perfluoroalkyl-3-iodo quinolines in Suzuki, annulation, dehalogenation and carboxylation reactions. Antimalarial activity of the 2-perfluoroalkyl-3-iodoquinolines is discussed.

Graphical abstract: Synthesis of highly substituted 2-perfluoroalkyl quinolines by electrophilic iodocyclization of perfluoroalkyl propargyl imines/amines

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Publication details

The article was received on 09 Sep 2008, accepted on 15 Oct 2008 and first published on 10 Nov 2008


Article type: Paper
DOI: 10.1039/B815398A
Citation: Org. Biomol. Chem., 2009,7, 85-93

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    Synthesis of highly substituted 2-perfluoroalkyl quinolines by electrophilic iodocyclization of perfluoroalkyl propargyl imines/amines

    P. R. Likhar, M. S. Subhas, S. Roy, M. L. Kantam, B. Sridhar, R. K. Seth and S. Biswas, Org. Biomol. Chem., 2009, 7, 85
    DOI: 10.1039/B815398A

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