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Issue 27, 2017
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Synthesis of 3-(2-thiopyridyl)indoles via the ruthenium catalyzed [2 + 2 + 2] cycloaddition of diynes and 3-thiocyanatoindoles

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Abstract

A highly efficient protocol for the synthesis of 3-(2-thiopyridyl)indoles via the ruthenium(II) catalyzed [2 + 2 + 2] cycloaddition reaction of α,ω-diynes with 3-thiocyanatoindoles under mild reaction conditions has been developed. A variety of 3-(2-thiopyridyl)indole derivatives were prepared by the reaction of the aforesaid substrates in the presence of a readily available chloro(pentamethylcyclopentadienyl)(cyclooctadiyne)ruthenium(II) catalyst in ethanol with good to excellent yields. This atom economical methodology provides us efficient access to 3-(2-thiopyridyl)indole skeletons with close structural similarity to other pyridyl indole thioethers that have potential medicinal value.

Graphical abstract: Synthesis of 3-(2-thiopyridyl)indoles via the ruthenium catalyzed [2 + 2 + 2] cycloaddition of diynes and 3-thiocyanatoindoles

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Publication details

The article was received on 05 May 2017, accepted on 16 Jun 2017 and first published on 16 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01101F
Citation: Org. Biomol. Chem., 2017,15, 5824-5830
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    Synthesis of 3-(2-thiopyridyl)indoles via the ruthenium catalyzed [2 + 2 + 2] cycloaddition of diynes and 3-thiocyanatoindoles

    H. Chowdhury and A. Goswami, Org. Biomol. Chem., 2017, 15, 5824
    DOI: 10.1039/C7OB01101F

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