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- Title
Conjugate Addition of Grignard Reagents to Thiochromones Catalyzed by Copper Salts: A Unified Approach to Both 2-Alkylthiochroman-4-One and Thioflavanone.
- Authors
Bellinger, Tania J.; Harvin, Teavian; Pickens-Flynn, Ti'Bran; Austin, Nataleigh; Whitaker, Samuel H.; Tang Yuk Tutein, Mai Ling C.; Hukins, Dabria T.; Deese, Nichele; Guo, Fenghai; Dembinski, Roman; Alabugin, Igor
- Abstract
Grignard reagents undergo conjugate addition to thiochromones catalyzed by copper salts to afford 2-substituted-thiochroman-4-ones, both 2-alkylthiochroman-4-ones and thioflavanones (2-arylthiochroman-4-ones), in good yields with trimethylsilyl chloride (TMSCl) as an additive. The best yields of 1,4-adducts can be attained with CuCN∙2LiCl as the copper source. Excellent yields of 2-alkyl-substituted thiochroman-4-ones and thioflavanones (2-aryl substituted) are attained with a broad range of Grignard reagents. This approach works well with both alkyl and aromatic Grignard reagents, thus providing a unified synthetic approach to privileged 2-substituted thiochroman-4-ones and a potential valuable precursor for further synthetic applications towards many pharmaceutically active molecules. The use of commercially available and/or readily prepared Grignard reagents will expedite the synthesis of a large library of both 2-alkyl substituted thiochroman-4-ones and thioflavanones for additional synthetic applications.
- Subjects
GRIGNARD reagents; CONJUGATE addition reactions; COPPER salts
- Publication
Molecules, 2020, Vol 25, Issue 9, p2128
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules25092128