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A novel method for the synthesis of haloisoquinolines involving an electrophile-exchange process

Posted on 24. November, 2014.

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Isoquinolines are present in a wide variety of biologically active compounds and pharmaceutical agents. Haloisoquinolins have recently attracted considerable attention from both industry and academia due to their therapeutic value in a variety of diseases, showing anti-HIV-1, anticancer, antimicrobial, and antifungalproperties.

Furthermore, functionalised isoquinolines have been shown to be organocatalysts and are recognised as useful tools for the highly enantioselective syntheses of chiral molecules. Because of their importance, the development of new synthetic approaches for their preparation remains an active research area.

A synthesis of haloisoquinolines through electrophilic cyclisation involving an electrophilic-exchange process has been developed. A variety of 2-alkynyl benzyl azides are cyclised in the presence of KX (X= I, Br, Cl) and electrophilic fluoride reagents,to afford the corresponding haloisoquinolines in moderate to good yields. Reagents for electrophilic halogenation have been generated from their inorganic salts (M+X) by oxidation with a Selectfluor reagent and reacted in situ with the substrates.

Read the full article in Journal of Chemical Research, Volume 38, Number 11, November 2014, pp. 639-700, pp. 682-685.

Authors: Hong-Ping Zhang and Hong-Yan Li
Department of Biology and Chemistry Engineering, Shaoyang University, Shaoyang 422000, P.R. China
Keywords: haloisoquinolines; electrophilic-exchange process; electrophilic cyclisation; 2-alkynyl benzyl azides