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Molecules 2018, 23(7), 1728; https://doi.org/10.3390/molecules23071728

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

1
Department of Chemistry, Winston Salem State University, 601 S. Martin Luther King Jr. Dr., Winston Salem, NC 27110, USA
2
Biomedical Research Infrastructure Center, Winston Salem State University, Winston Salem, NC 27110, USA
*
Author to whom correspondence should be addressed.
Received: 16 June 2018 / Revised: 5 July 2018 / Accepted: 13 July 2018 / Published: 15 July 2018
(This article belongs to the Special Issue Organometallic Catalysis in Organic Synthesis)
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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. View Full-Text
Keywords: thiochroman-4-ones; conjugate addition; lithium dialkyl cuprates; thiochromones; 2-alkylthiochroman-4-ones thiochroman-4-ones; conjugate addition; lithium dialkyl cuprates; thiochromones; 2-alkylthiochroman-4-ones
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Bass, S.A.; Parker, D.M.; Bellinger, T.J.; Eaton, A.S.; Dibble, A.S.; Koroma, K.L.; Sekyi, S.A.; Pollard, D.A.; Guo, F. Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications. Molecules 2018, 23, 1728.

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