Discipline: Chemistry and Chemical Sciences
Subcategory: Chemistry (not Biochemistry)
Shekinah Bass - Winston-Salem State University
Co-Author(s): Tania Bellinger, Winston Salem State University, Winston Salem, NC ; Fenghai Guo, Winston Salem State University, Winston Salem, NC
Thiochromones undergo conjugate addition reactions with alkylcuprates to afford thiochromanones (2-alkyl substituted thiochroman-4-ones), providing an efficient synthetic approach to privileged sulfur-containing structural motifs and valuable precursor for many pharmaceuticals. Excellent yields of 2-alkyl substituted thiochroman-4-ones can be attained with lithium dialkylcuprates, lithium alkylcyanocuprates and Grignard reagents with copper catalysis. This method provides a rapid entry to a variety of thiochromanones in excellent yields (up to 88%). The use of commercially available or easily prepared organometallic reagents will expedite the synthesis of a large library of thiochromanone and derivatives for further synthetic applications and biological studies.
Funder Acknowledgement(s): NSF HBCU-UP research initiation award (award no. 1600987).
Faculty Advisor: Fenghai Guo, email@example.com
Role: I developed the organocuprate mediated 1-4 conjugate addition of Grignard Reagents to thiochromones. Investigated the effect of alkyl groups and different types of copper salts and solvent effects on the substituted thiochromone. Both substituted and non-substituted thiochromones were investigated. I also synthesized a variety of bioactive 2-substituted thiochromanones. Thiochromanones are key intermediates for bioactive products such as sulfoxides. Currently, I am working on making other bioactive products such as sulfoxides and sulfones. Recently I just published some of these results in a paper.