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

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...

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Autores principales: Bass, Shekinah A., Parker, Dynasty M., Bellinger, Tania J., Eaton, Aireal S., Dibble, Angelica S., Koroma, Kaata L., Sekyi, Sylvia A., Pollard, David A., Guo, Fenghai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6099951/
https://www.ncbi.nlm.nih.gov/pubmed/30011953
http://dx.doi.org/10.3390/molecules23071728
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author Bass, Shekinah A.
Parker, Dynasty M.
Bellinger, Tania J.
Eaton, Aireal S.
Dibble, Angelica S.
Koroma, Kaata L.
Sekyi, Sylvia A.
Pollard, David A.
Guo, Fenghai
author_facet Bass, Shekinah A.
Parker, Dynasty M.
Bellinger, Tania J.
Eaton, Aireal S.
Dibble, Angelica S.
Koroma, Kaata L.
Sekyi, Sylvia A.
Pollard, David A.
Guo, Fenghai
author_sort Bass, Shekinah A.
collection PubMed
description 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.
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spelling pubmed-60999512018-11-13 Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications Bass, Shekinah A. Parker, Dynasty M. Bellinger, Tania J. Eaton, Aireal S. Dibble, Angelica S. Koroma, Kaata L. Sekyi, Sylvia A. Pollard, David A. Guo, Fenghai Molecules Article 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. MDPI 2018-07-15 /pmc/articles/PMC6099951/ /pubmed/30011953 http://dx.doi.org/10.3390/molecules23071728 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Bass, Shekinah A.
Parker, Dynasty M.
Bellinger, Tania J.
Eaton, Aireal S.
Dibble, Angelica S.
Koroma, Kaata L.
Sekyi, Sylvia A.
Pollard, David A.
Guo, Fenghai
Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications
title Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications
title_full Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications
title_fullStr Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications
title_full_unstemmed Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications
title_short Development of Conjugate Addition of Lithium Dialkylcuprates to Thiochromones: Synthesis of 2-Alkylthiochroman-4-ones and Additional Synthetic Applications
title_sort development of conjugate addition of lithium dialkylcuprates to thiochromones: synthesis of 2-alkylthiochroman-4-ones and additional synthetic applications
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6099951/
https://www.ncbi.nlm.nih.gov/pubmed/30011953
http://dx.doi.org/10.3390/molecules23071728
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