A New Method for the Synthesis of 3-Thiocyanatopyrazolo[1,5-a]pyrimidines

In this article, we demonstrate how an original effective “metal-free” and “chromatography-free” route for the synthesis of 3-thiocyanatopyrazolo[1,5-a]pyrimidines has been developed. It is based on electrooxidative (anodic) C–H thiocyanation of 5-aminopyrazoles by thiocyanate ion leading to 4-thioc...

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Autores principales: Kokorekin, Vladimir A., Neverov, Sergey V., Kuzina, Vera N., Petrosyan, Vladimir A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7570695/
https://www.ncbi.nlm.nih.gov/pubmed/32933044
http://dx.doi.org/10.3390/molecules25184169
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author Kokorekin, Vladimir A.
Neverov, Sergey V.
Kuzina, Vera N.
Petrosyan, Vladimir A.
author_facet Kokorekin, Vladimir A.
Neverov, Sergey V.
Kuzina, Vera N.
Petrosyan, Vladimir A.
author_sort Kokorekin, Vladimir A.
collection PubMed
description In this article, we demonstrate how an original effective “metal-free” and “chromatography-free” route for the synthesis of 3-thiocyanatopyrazolo[1,5-a]pyrimidines has been developed. It is based on electrooxidative (anodic) C–H thiocyanation of 5-aminopyrazoles by thiocyanate ion leading to 4-thiocyanato-5-aminopyrazoles (stage 1, yields up to 87%) following by their chemical condensation with 1,3-dicarbonyl compounds or their derivatives (stage 2, yields up to 96%). This method is equally effective for the synthesis of 3-thiocyanatopyrazolo[1,5-a]pyrimidines, both without substituents and with various donor (acceptor) substituents in the pyrimidine ring.
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spelling pubmed-75706952020-10-28 A New Method for the Synthesis of 3-Thiocyanatopyrazolo[1,5-a]pyrimidines Kokorekin, Vladimir A. Neverov, Sergey V. Kuzina, Vera N. Petrosyan, Vladimir A. Molecules Article In this article, we demonstrate how an original effective “metal-free” and “chromatography-free” route for the synthesis of 3-thiocyanatopyrazolo[1,5-a]pyrimidines has been developed. It is based on electrooxidative (anodic) C–H thiocyanation of 5-aminopyrazoles by thiocyanate ion leading to 4-thiocyanato-5-aminopyrazoles (stage 1, yields up to 87%) following by their chemical condensation with 1,3-dicarbonyl compounds or their derivatives (stage 2, yields up to 96%). This method is equally effective for the synthesis of 3-thiocyanatopyrazolo[1,5-a]pyrimidines, both without substituents and with various donor (acceptor) substituents in the pyrimidine ring. MDPI 2020-09-11 /pmc/articles/PMC7570695/ /pubmed/32933044 http://dx.doi.org/10.3390/molecules25184169 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
Kokorekin, Vladimir A.
Neverov, Sergey V.
Kuzina, Vera N.
Petrosyan, Vladimir A.
A New Method for the Synthesis of 3-Thiocyanatopyrazolo[1,5-a]pyrimidines
title A New Method for the Synthesis of 3-Thiocyanatopyrazolo[1,5-a]pyrimidines
title_full A New Method for the Synthesis of 3-Thiocyanatopyrazolo[1,5-a]pyrimidines
title_fullStr A New Method for the Synthesis of 3-Thiocyanatopyrazolo[1,5-a]pyrimidines
title_full_unstemmed A New Method for the Synthesis of 3-Thiocyanatopyrazolo[1,5-a]pyrimidines
title_short A New Method for the Synthesis of 3-Thiocyanatopyrazolo[1,5-a]pyrimidines
title_sort new method for the synthesis of 3-thiocyanatopyrazolo[1,5-a]pyrimidines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7570695/
https://www.ncbi.nlm.nih.gov/pubmed/32933044
http://dx.doi.org/10.3390/molecules25184169
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