Catalyst-free synthesis of thiazolidines via sequential hydrolysis/rearrangement reactions of 5-arylidenethiazolidin-4-ones at room temperature. Issue 11 (28th February 2018)

• Record Type: Journal Article
• Authors: Zeng, Fanxun; Zhang, Letian; Shao, Xusheng; Li, Zhong; Xu, Xiaoyong
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 11(2018)
• Page Start: 1932
• Page End: 1938
• Publication Date: 2018-02-28
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob02924a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Functionalized thiazolidines were obtained via the 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.