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Issue 9, 2019
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A new strategy for the synthesis of pyridines from N-propargylic β-enaminothiones

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Abstract

A new method for the synthesis of 2,4,5-trisubstituted pyridines from N-propargylic β-enaminothiones is reported. β-Enaminothiones were prepared by thionation of the corresponding β-enaminones with Lawesson's reagent. When treated with diisopropylamine in DMF at room temperature, N-propargylic β-enaminothiones yielded 2,4,5-trisubstituted pyridines in moderate to high yields, along with small amounts of 2-methylene-2,3-dihydro-1,4-thiazepines. The reaction was found to be general for a broad range of N-propargylic β-enaminothiones and tolerated the presence of aromatic, heteroaromatic and aliphatic groups with electron-withdrawing and electron-donating substituents. The method could be widened to the internal alkyne-tethered N-propargylic β-enaminothiones. This operationally simple method may provide rapid access to a library of functionalized pyridines of pharmacological interest.

Graphical abstract: A new strategy for the synthesis of pyridines from N-propargylic β-enaminothiones

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Publication details

The article was received on 22 Dec 2018, accepted on 07 Feb 2019 and first published on 07 Feb 2019


Article type: Paper
DOI: 10.1039/C8OB03180K
Citation: Org. Biomol. Chem., 2019,17, 2529-2541

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    A new strategy for the synthesis of pyridines from N-propargylic β-enaminothiones

    Y. Kelgokmen and M. Zora, Org. Biomol. Chem., 2019, 17, 2529
    DOI: 10.1039/C8OB03180K

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