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

Organic & Biomolecular Chemistry
Fanxun ZengXiaoyong Xu

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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Citations

Aug 7, 2021·The Journal of Organic Chemistry·Laura SantosFrédéric R Leroux

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Methods Mentioned

BETA
column chromatography
X-ray

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