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Issue 24, 2016
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Solvent- and halide-free synthesis of pyridine-2-yl substituted ureas through facile C–H functionalization of pyridine N-oxides

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Abstract

A novel solvent- and halide-free atom-economical synthesis of practically useful pyridine-2-yl substituted ureas utilizes easily accessible or commercially available pyridine N-oxides (PyO) and dialkylcyanamides. The observed C–H functionalization of PyO is suitable for the good-to-high yielding synthesis of a wide range of pyridine-2-yl substituted ureas featuring electron donating and electron withdrawing, sensitive, or even fugitive functional groups at any position of the pyridine ring (63–92%; 19 examples). In the cases of 3-substituted PyO, the C–H functionalization occurs regioselectively providing a route for facile generation of ureas bearing a 5-substituted pyridine-2-yl moiety.

Graphical abstract: Solvent- and halide-free synthesis of pyridine-2-yl substituted ureas through facile C–H functionalization of pyridine N-oxides

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Publication details

The article was received on 12 Sep 2016, accepted on 05 Oct 2016, published on 07 Oct 2016 and first published online on 07 Oct 2016


Article type: Paper
DOI: 10.1039/C6GC02556K
Citation: Green Chem., 2016,18, 6630-6636
  • Open access: Creative Commons BY-NC license
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    Solvent- and halide-free synthesis of pyridine-2-yl substituted ureas through facile C–H functionalization of pyridine N-oxides

    V. A. Rassadin, D. P. Zimin, G. Z. Raskil'dina, A. Yu. Ivanov, V. P. Boyarskiy, S. S. Zlotskii and V. Yu. Kukushkin, Green Chem., 2016, 18, 6630
    DOI: 10.1039/C6GC02556K

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