Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives

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Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives. / Filimonov, Valeriy; Topchiy, Alexandra I.; Ilkin, Vladimir et al.
In: Beilstein Journal of Organic Chemistry, Vol. 19, 2023, p. 1191-1197.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{bb57a408a6e3406cb4bf728d88fc0ac6,

title = "Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives",

abstract = "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. {\textcopyright} 2023 Filimonov et al.",

author = "Valeriy Filimonov and Topchiy, {Alexandra I.} and Vladimir Ilkin and Tetyana Beryozkina and Vasiliy Bakulev",

note = "The authors thank the Russian Science Foundation (project 23-13-00248).",

year = "2023",

doi = "10.3762/bjoc.19.87",

language = "English",

volume = "19",

pages = "1191--1197",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

RIS

TY - JOUR

T1 - Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives

AU - Filimonov, Valeriy

AU - Topchiy, Alexandra I.

AU - Ilkin, Vladimir

AU - Beryozkina, Tetyana

AU - Bakulev, Vasiliy

N1 - The authors thank the Russian Science Foundation (project 23-13-00248).

PY - 2023

Y1 - 2023

N2 - 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. © 2023 Filimonov et al.

AB - 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. © 2023 Filimonov et al.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85169566909

U2 - 10.3762/bjoc.19.87

DO - 10.3762/bjoc.19.87

M3 - Article

VL - 19

SP - 1191

EP - 1197

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -

ID: 44669033