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Catalyst-free synthesis of thiazolidines via sequential hydrolysis/rearrangement reactions of 5-arylidenethiazolidin-4-ones at room temperature

Abstract

A catalyst-free sequential reaction involving hydrolysis and intramolecular aza-Michael addition was developed for synthesizing functionalized thiazolidines from 5-arylidenethiazolidin-4-ones at room temperature. A series of thiazolidine-5-carboxylic acids were prepared in good to excellent yields (up to 97% yield) and excellent diastereoselectivities (up to >20:1 dr). This methodology was applicable to the construction of derivatives of thiacloprid and flutianil with good yields.

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Publication details

The article was received on 27 Nov 2017, accepted on 06 Feb 2018 and first published on 06 Feb 2018


Article type: Paper
DOI: 10.1039/C7OB02924A
Citation: Org. Biomol. Chem., 2018, Accepted Manuscript
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    Catalyst-free synthesis of thiazolidines via sequential hydrolysis/rearrangement reactions of 5-arylidenethiazolidin-4-ones at room temperature

    F. Zeng, L. Zhang, X. Shao, Z. Li and X. Xu, Org. Biomol. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C7OB02924A

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