Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications

Shekinah A Bass; Dynasty M Parker; Tania J Bellinger; Aireal S Eaton; Angelica S Dibble; Kaata L Koroma; Sylvia A Sekyi; David A Pollard; Fenghai Guo

doi:10.3390/molecules23071728

Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications

Molecules. 2018 Jul 15;23(7):1728. doi: 10.3390/molecules23071728.

Authors

Shekinah A Bass¹, Dynasty M Parker², Tania J Bellinger³, Aireal S Eaton⁴, Angelica S Dibble⁵, Kaata L Koroma⁶, Sylvia A Sekyi⁷, David A Pollard⁸, Fenghai Guo^{9

10}

Affiliations

¹ Department of Chemistry, Winston Salem State University, 601 S. Martin Luther King Jr. Dr., Winston Salem, NC 27110, USA. sbass116@rams.wssu.edu.
² Department of Chemistry, Winston Salem State University, 601 S. Martin Luther King Jr. Dr., Winston Salem, NC 27110, USA. dparker115@rams.wssu.edu.
³ Department of Chemistry, Winston Salem State University, 601 S. Martin Luther King Jr. Dr., Winston Salem, NC 27110, USA. tbellinger115@rams.wssu.edu.
⁴ Department of Chemistry, Winston Salem State University, 601 S. Martin Luther King Jr. Dr., Winston Salem, NC 27110, USA. aeaton114@rams.wssu.edu.
⁵ Department of Chemistry, Winston Salem State University, 601 S. Martin Luther King Jr. Dr., Winston Salem, NC 27110, USA. adibble114@rams.wssu.edu.
⁶ Department of Chemistry, Winston Salem State University, 601 S. Martin Luther King Jr. Dr., Winston Salem, NC 27110, USA. kkoroma116@rams.wssu.edu.
⁷ Department of Chemistry, Winston Salem State University, 601 S. Martin Luther King Jr. Dr., Winston Salem, NC 27110, USA. ssekyi116@rams.wssu.edu.
⁸ Department of Chemistry, Winston Salem State University, 601 S. Martin Luther King Jr. Dr., Winston Salem, NC 27110, USA. pollardda@wssu.edu.
⁹ Department of Chemistry, Winston Salem State University, 601 S. Martin Luther King Jr. Dr., Winston Salem, NC 27110, USA. guof@wssu.edu.
¹⁰ Biomedical Research Infrastructure Center, Winston Salem State University, Winston Salem, NC 27110, USA. guof@wssu.edu.

Abstract

Lithium dialkylcuprates undergo conjugate addition to thiochromones to afford 2-alkylthiochroman-4-ones in good yields. This approach provide an efficient and general synthetic approach to privileged sulfur-containing structural motifs and valuable precursors for many pharmaceuticals, starting from common substrates-thiochromones. Good yields of 2-alkyl-substituted thiochroman-4-ones are attained with lithium dialkylcuprates, lithium alkylcyanocuprates or substoichiometric amount of copper salts. The use of commercially available inexpensive alkyllithium reagents will expedite the synthesis of a large library of 2-alkyl substituted thiochroman-4-ones for additional synthetic applications.

Keywords: 2-alkylthiochroman-4-ones; conjugate addition; lithium dialkyl cuprates; thiochroman-4-ones; thiochromones.

MeSH terms

Chromones* / chemical synthesis
Chromones* / chemistry
Copper / chemistry*
Lithium / chemistry*
Organometallic Compounds / chemistry*

Substances

Chromones
Organometallic Compounds
Copper
Lithium

Grants and funding

R25 GM113774/GM/NIGMS NIH HHS/United States