Cargando…
Trifluoromethoxypyrazines: Preparation and Properties
The incorporation of the trifluoromethoxy group into organic molecules has become very popular due to the unique properties of the named substituent that has a “pseudohalogen” character, while the chemical properties of the synthesized compound, especially heterocycles with such a group, are less st...
Autores principales: | , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7248996/ https://www.ncbi.nlm.nih.gov/pubmed/32397388 http://dx.doi.org/10.3390/molecules25092226 |
_version_ | 1783538501029986304 |
---|---|
author | Sokolenko, Taras M. Yagupolskii, Yurii L. |
author_facet | Sokolenko, Taras M. Yagupolskii, Yurii L. |
author_sort | Sokolenko, Taras M. |
collection | PubMed |
description | The incorporation of the trifluoromethoxy group into organic molecules has become very popular due to the unique properties of the named substituent that has a “pseudohalogen” character, while the chemical properties of the synthesized compound, especially heterocycles with such a group, are less studied. As trifluoromethoxy-substituted pyrazines are still unknown, we have developed efficient and scalable methods for 2-chloro-5-trifluoromethoxypyrazine synthesis, showing the synthetic utility of this molecule for Buchwald-Hartwig amination and the Kumada-Corriu and Suzuki and Sonogashira coupling reactions. Some comparisons of chlorine atom and trifluoromethoxy group stability in these transformations have been carried out. |
format | Online Article Text |
id | pubmed-7248996 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-72489962020-06-10 Trifluoromethoxypyrazines: Preparation and Properties Sokolenko, Taras M. Yagupolskii, Yurii L. Molecules Article The incorporation of the trifluoromethoxy group into organic molecules has become very popular due to the unique properties of the named substituent that has a “pseudohalogen” character, while the chemical properties of the synthesized compound, especially heterocycles with such a group, are less studied. As trifluoromethoxy-substituted pyrazines are still unknown, we have developed efficient and scalable methods for 2-chloro-5-trifluoromethoxypyrazine synthesis, showing the synthetic utility of this molecule for Buchwald-Hartwig amination and the Kumada-Corriu and Suzuki and Sonogashira coupling reactions. Some comparisons of chlorine atom and trifluoromethoxy group stability in these transformations have been carried out. MDPI 2020-05-09 /pmc/articles/PMC7248996/ /pubmed/32397388 http://dx.doi.org/10.3390/molecules25092226 Text en © 2020 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 Sokolenko, Taras M. Yagupolskii, Yurii L. Trifluoromethoxypyrazines: Preparation and Properties |
title | Trifluoromethoxypyrazines: Preparation and Properties |
title_full | Trifluoromethoxypyrazines: Preparation and Properties |
title_fullStr | Trifluoromethoxypyrazines: Preparation and Properties |
title_full_unstemmed | Trifluoromethoxypyrazines: Preparation and Properties |
title_short | Trifluoromethoxypyrazines: Preparation and Properties |
title_sort | trifluoromethoxypyrazines: preparation and properties |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7248996/ https://www.ncbi.nlm.nih.gov/pubmed/32397388 http://dx.doi.org/10.3390/molecules25092226 |
work_keys_str_mv | AT sokolenkotarasm trifluoromethoxypyrazinespreparationandproperties AT yagupolskiiyuriil trifluoromethoxypyrazinespreparationandproperties |