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Metal-catalyzed synthesis of five-membered ring N-heterocycles. A recent update

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Chemistry of Heterocyclic Compounds Aims and scope

The review deals with the metal-catalyzed synthetic methods used for the construction of 5-membered nitrogen-containing aromatic and nonaromatic heterocycles with one to three nitrogen atoms, published in the years 2008–2017. The methodology is based on the metalcatalyzed activation of the alkyl C(sp3)–H, alkenyl C(sp2)–H, and terminal alkyne C(sp)–H bonds of appropriate precursors in order to perform intermolecular and intramolecular reactions. These bond forming reactions include C(sp3)–C(sp2), C(sp2)–C(sp2), and C(sp2)–C(sp) coupling, hydroamination at C(sp2)–H and C(sp)–H bonds, and oxidative amination of alkyl C(sp3)–H, alkenyl and arene C(sp2)–H, and terminal alkyne C(sp)–H bonds. Two further bond forming methods are intramolecular nitrenoid–arene C(sp2) coupling and cycloaddition reactions. Transition metals are systematically used in these synthetic methods, and only in a few cases Lewis acids are used as catalysts. In general, the metal-catalyzed cyclizations leading to five-membered heterocycles are very efficient and particularly useful in the synthesis of natural and unnatural biologically active products.

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  1. Section of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, P. O. Box 1186, 451 10, Ioannina, Greece

    George Varvounis, Ioannis E. Gerontitis & Vasileios Gkalpinos

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  1. George Varvounis
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(3), 249–268

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Varvounis, G., Gerontitis, I.E. & Gkalpinos, V. Metal-catalyzed synthesis of five-membered ring N-heterocycles. A recent update. Chem Heterocycl Comp 54, 249–268 (2018). https://doi.org/10.1007/s10593-018-2260-8

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