Synthesis of N‑Aryl-4-trifluoromethylthiazol-2-amines via Insertion/Annulation of Trifluoromethylimidoyl Sulfoxonium Ylides with Sodium Thiocyanate

An efficient p-TsOH-mediated insertion of sodium thiocyanate into trifluoromethylimidoyl sulfoxonium ylides has been reported, affording annulated N-aryl-4-trifluoromethylthiazol-2-amines in 42–84% yields in a one-pot manner. This protocol encompasses a variety of trifluoromethylimidoyl sulfoxonium...

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Published inJournal of organic chemistry Vol. 89; no. 17; pp. 12255 - 12262
Main Authors Ding, Yuhao, Liu, Yaopeng, Ge, Jin, Wu, Xi, Li, Zhenghao, Cheng, Guolin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.09.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
moieties
organic chemistry
Physical Sciences
Science & Technology
sodium
thiazoles
thiocyanates
INSERTION
2-AMINOTHIAZOLES
CONSTRUCTION
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Summary:An efficient p-TsOH-mediated insertion of sodium thiocyanate into trifluoromethylimidoyl sulfoxonium ylides has been reported, affording annulated N-aryl-4-trifluoromethylthiazol-2-amines in 42–84% yields in a one-pot manner. This protocol encompasses a variety of trifluoromethylimidoyl sulfoxonium ylides with thiocyanate serving as the source of the “S–CN” moiety of the thiazole ring. The versatile transformations of the resulting pharmacologically important N-aryl-4-trifluoromethylthiazol-2-amines were also demonstrated.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01199