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Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives

It was shown that the reaction of 2-cyanothioacetamides with hydrazine involves both cyano- and thioamide groups, and 3,5-diaminopyrazoles are formed. In the reaction of 2-cyano-3-(dimethylamino)-N,N-dimethylprop-2-enethioamides with hydrazine and its derivatives, the interaction proceeds with the p...

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Autores principales: Filimonov, Valeriy O, Topchiy, Alexandra I, Ilkin, Vladimir G, Beryozkina, Tetyana V, Bakulev, Vasiliy A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10428587/
https://www.ncbi.nlm.nih.gov/pubmed/37592935
http://dx.doi.org/10.3762/bjoc.19.87
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author Filimonov, Valeriy O
Topchiy, Alexandra I
Ilkin, Vladimir G
Beryozkina, Tetyana V
Bakulev, Vasiliy A
author_facet Filimonov, Valeriy O
Topchiy, Alexandra I
Ilkin, Vladimir G
Beryozkina, Tetyana V
Bakulev, Vasiliy A
author_sort Filimonov, Valeriy O
collection PubMed
description It was shown that the reaction of 2-cyanothioacetamides with hydrazine involves both cyano- and thioamide groups, and 3,5-diaminopyrazoles are formed. In the reaction of 2-cyano-3-(dimethylamino)-N,N-dimethylprop-2-enethioamides with hydrazine and its derivatives, the interaction proceeds with the participation of cyano- and enamine groups, not affecting the thiocarbamoyl group, and leads to the formation of 4-thiocarbamoylpyrazoles. A synthesis method has been developed and a series of 1-substituted-4-thiocarbamoyl pyrazoles has been thus synthesized. The structure of the reaction products was studied using NMR spectroscopy and mass spectrometry and confirmed by X-ray diffraction analysis.
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spelling pubmed-104285872023-08-17 Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives Filimonov, Valeriy O Topchiy, Alexandra I Ilkin, Vladimir G Beryozkina, Tetyana V Bakulev, Vasiliy A Beilstein J Org Chem Full Research Paper It was shown that the reaction of 2-cyanothioacetamides with hydrazine involves both cyano- and thioamide groups, and 3,5-diaminopyrazoles are formed. In the reaction of 2-cyano-3-(dimethylamino)-N,N-dimethylprop-2-enethioamides with hydrazine and its derivatives, the interaction proceeds with the participation of cyano- and enamine groups, not affecting the thiocarbamoyl group, and leads to the formation of 4-thiocarbamoylpyrazoles. A synthesis method has been developed and a series of 1-substituted-4-thiocarbamoyl pyrazoles has been thus synthesized. The structure of the reaction products was studied using NMR spectroscopy and mass spectrometry and confirmed by X-ray diffraction analysis. Beilstein-Institut 2023-08-08 /pmc/articles/PMC10428587/ /pubmed/37592935 http://dx.doi.org/10.3762/bjoc.19.87 Text en Copyright © 2023, Filimonov et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Filimonov, Valeriy O
Topchiy, Alexandra I
Ilkin, Vladimir G
Beryozkina, Tetyana V
Bakulev, Vasiliy A
Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives
title Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives
title_full Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives
title_fullStr Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives
title_full_unstemmed Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives
title_short Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives
title_sort cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10428587/
https://www.ncbi.nlm.nih.gov/pubmed/37592935
http://dx.doi.org/10.3762/bjoc.19.87
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