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Issue 8, 2019
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Iodine-promoted radical alkyl sulfuration of imidazopyridines with dialkyl azo compounds and elemental sulfur

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Abstract

Dialkyl azo compounds were found to be effective alkyl radical sources for direct alkyl sulfuration with imidazopyridines using elemental sulfur under metal-free conditions. Iodine, an inexpensive and mild reagent, could promote alkyl sulfuration. A variety of quaternary cyanoalkyl radicals were successfully coupled with elemental sulfur. A subsequent C–H sulfuration of imidazopyridines afforded a diverse array of imidazopyridine derivatives bearing cyanoalkylthio groups. The cyano group could be modified and further underwent condensation with 2-aminothiazole to afford an interesting heterocyclic amide. Control experiments showed that iodine could greatly suppress the self-coupling of cyanoalkyl radicals, thus making the sulfuration proceed smoothly.

Graphical abstract: Iodine-promoted radical alkyl sulfuration of imidazopyridines with dialkyl azo compounds and elemental sulfur

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Publication details

The article was received on 24 Dec 2018, accepted on 31 Jan 2019 and first published on 01 Feb 2019


Article type: Paper
DOI: 10.1039/C8OB03191F
Citation: Org. Biomol. Chem., 2019,17, 2279-2286

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    Iodine-promoted radical alkyl sulfuration of imidazopyridines with dialkyl azo compounds and elemental sulfur

    Y. Gao, Z. Huang, L. Xu, Z. Li, Z. Lai and R. Tang, Org. Biomol. Chem., 2019, 17, 2279
    DOI: 10.1039/C8OB03191F

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