Michael Addition of Aryl Thiols to 3-(2,2,2-Trifluoroethylidene)Oxindoles under Catalyst-Free Conditions: The Rapid Synthesis of Sulfur-Containing Oxindole Derivatives

A mild and efficient catalyst-free method for the rapid synthesis at room temperature of 3-thiomethylated oxindole derivatives has been achieved via the Michael addition of aryl thiols to ring and 1-substituted 3-(2,2,2-trifluoroethylidene)oxindoles in dichloromethane. The method was applicable to a...

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Bibliographic Details
Published inJournal of chemical research Vol. 42; no. 4; pp. 210 - 214
Main Authors Chen, Bo, Lei, Jiaheng, Zhao, Junling
Format Journal Article
LanguageEnglish
Published London, England SAGE Publications 01.04.2018
Science Reviews 2000 Ltd
Sage Publications Ltd
Subjects
Aromatic compounds
Catalysis
Catalysts
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Derivatives
Dichloromethane
Physical Sciences
Science & Technology
Substitutes
Thiols
Michael addition
3-(2,2,2-trifluoroethylidene)oxindole
diastereoselectivity
aryl thiols
catalyst free synthesis
ASYMMETRIC-SYNTHESIS
FLUORINATION
TRIFLUOROMETHYLATION
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Summary:A mild and efficient catalyst-free method for the rapid synthesis at room temperature of 3-thiomethylated oxindole derivatives has been achieved via the Michael addition of aryl thiols to ring and 1-substituted 3-(2,2,2-trifluoroethylidene)oxindoles in dichloromethane. The method was applicable to a wide range of thiols and variously substituted 3-(2,2,2-trifluoroethylidene)oxindoles under mild conditions as demonstrated by the synthesis in high yields with good diastereoselectivities of 30 3-thiomethylated oxindoles bearing a trifluoromethyl group.
ISSN:1747-5198
2047-6507
DOI:10.3184/174751918X15240724383170