Preference of cis-Thioamide Structure in N‑Thioacyl‑N‑methylanilines

The thioamide group represents a highly attractive isostere of the amide bond. We report a combined structural and computational study on cis-thioamide conformation of N-thioacyl-N-methylanilines. Amide to thioamide replacement in a class of anilides that are highly valuable as conformational locks...

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Bibliographic Details
Published in:Organic letters 2020-12, Vol.22 (24), p.9500-9505
Main Authors: Zhang, Jin, Liu, Zhulin, Yin, Zheng, Yang, Xiufang, Ma, Yangmin, Szostak, Roman, Szostak, Michal
Format: Article
Language:English
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Summary:The thioamide group represents a highly attractive isostere of the amide bond. We report a combined structural and computational study on cis-thioamide conformation of N-thioacyl-N-methylanilines. Amide to thioamide replacement in a class of anilides that are highly valuable as conformational locks results in a higher preference for cis conformation in a unique compacted template intrinsic to the thioamide structure. The study strongly supports the use of N-methylthioanilides as cis-conformational locks in various facets of chemistry.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03512