Cargando…
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...
Autores principales: | , , , , , , , , |
---|---|
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 |
_version_ | 1783348767079006208 |
---|---|
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. |
format | Online Article Text |
id | pubmed-6099951 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT bassshekinaha developmentofconjugateadditionoflithiumdialkylcupratestothiochromonessynthesisof2alkylthiochroman4onesandadditionalsyntheticapplications AT parkerdynastym developmentofconjugateadditionoflithiumdialkylcupratestothiochromonessynthesisof2alkylthiochroman4onesandadditionalsyntheticapplications AT bellingertaniaj developmentofconjugateadditionoflithiumdialkylcupratestothiochromonessynthesisof2alkylthiochroman4onesandadditionalsyntheticapplications AT eatonaireals developmentofconjugateadditionoflithiumdialkylcupratestothiochromonessynthesisof2alkylthiochroman4onesandadditionalsyntheticapplications AT dibbleangelicas developmentofconjugateadditionoflithiumdialkylcupratestothiochromonessynthesisof2alkylthiochroman4onesandadditionalsyntheticapplications AT koromakaatal developmentofconjugateadditionoflithiumdialkylcupratestothiochromonessynthesisof2alkylthiochroman4onesandadditionalsyntheticapplications AT sekyisylviaa developmentofconjugateadditionoflithiumdialkylcupratestothiochromonessynthesisof2alkylthiochroman4onesandadditionalsyntheticapplications AT pollarddavida developmentofconjugateadditionoflithiumdialkylcupratestothiochromonessynthesisof2alkylthiochroman4onesandadditionalsyntheticapplications AT guofenghai developmentofconjugateadditionoflithiumdialkylcupratestothiochromonessynthesisof2alkylthiochroman4onesandadditionalsyntheticapplications |