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Issue 6, 2018
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Base-promoted ring opening of 3-chlorooxindoles for the construction of 2-aminoarylthioates and their transformation to quinazolin-4(3H)-ones

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Abstract

An unprecedented methodology for the preparation of diverse S-alkyl 2-aminoarylthioates has been developed based on cesium carbonate-promoted direct ring opening of 3-chlorooxindoles with thiols. This novel protocol proceeds via cascade sulfenylation, aerial oxidation, C2–C3 bond cleavage, and decarboxylation. The resulting products from this transformation exhibit potential for application as fluorescent sensors for the detection of Fe3+ ions. In addition, this methodology provides a concise pathway for the construction of a variety of biologically interesting quinazolin-4(3H)-ones in good yields.

Graphical abstract: Base-promoted ring opening of 3-chlorooxindoles for the construction of 2-aminoarylthioates and their transformation to quinazolin-4(3H)-ones

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Publication details

The article was received on 12 Jan 2018, accepted on 22 Feb 2018 and first published on 01 Mar 2018


Article type: Paper
DOI: 10.1039/C8NJ00195B
Citation: New J. Chem., 2018,42, 4735-4741

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    Base-promoted ring opening of 3-chlorooxindoles for the construction of 2-aminoarylthioates and their transformation to quinazolin-4(3H)-ones

    T. N. Poudel, H. D. Khanal and Y. R. Lee, New J. Chem., 2018, 42, 4735
    DOI: 10.1039/C8NJ00195B

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