A rapid entry into thioflavanones via conjugate additions of diarylcuprates to thiochromones

TETRAHEDRON

卷:73

Article

Guo, Fenghai^1,2  Jeffries, Malcolm C.¹  Graves, Briana N.¹  Graham, Shekinah A.¹  Pollard, David A.¹  Pang, Gehao¹  Chen, Henry Y.¹ 

[1] Winston Salem State Univ, Dept Chem, 601 S Martin Luther King Jr Dr, Winston Salem, NC 27110 USA

[2] Winston Salem State Univ, Biomed Res Infrastruct Ctr, 601 S Martin Luther King Jr Dr, Winston Salem, NC 27110 USA

关键词: Thioflavanones;    Conjugate addition;    Organocuprates;    Thiochromones;    Organometallic;   

DOI  :  10.1016/j.tet.2017.08.012

来源: Elsevier

【 摘 要 】

Thiochromone undergo conjugate addition reactions with arylcuprates to afford 2-substituted thioflavanones, providing an efficient synthetic approach to privileged sulfur-containing structural motifs and valuable precursor for many pharmaceuticals. Excellent yields of substituted thioflavanones are achieved with lithium diarylcuprates, lithium arylcyanocuprates and Grignard reagents with copper catalysis. This method provides a rapid entry to a variety of thioflavanones in excellent yields (up to 92%). The use of commercially available or easily prepared organometallic reagents will expedite the synthesis of a large library of thioflavanones for further synthetic applications and biological studies. (C) 2017 Elsevier Ltd. All rights reserved.

【 授权许可】

Free