First N‐Functionalization of 4‐Nitroso‐1H‐Pyrazoles Using Monofunctional and Bifunctional Alkylating Agents

Author:

Bobrova Anastasiia V.1ORCID,Krasnov Pavel O.2ORCID,Radzhabov Amirbek D.3ORCID,Kondrasenko Alexander A.4ORCID,Root Evgeniy V.15ORCID,Suboch Georgii A.1ORCID

Affiliation:

1. Department of Organic Chemistry and Technology of Organic Substances Reshetnev Siberian State University of Science and Technology 31, Krasnoyarskii Rabochii prospekt Krasnoyarsk 660037 Russian Federation

2. International Research Center of Spectroscopy and Quantum Chemistry Siberian Federal University 26, Kirensky str. Krasnoyarsk 660074 Russian Federation

3. Research School of Chemistry and Applied Biomedical Sciences Tomsk Polytechnic University 30, Lenina Av. Tomsk 634050 Russian Federation

4. Laboratory of Molecular Spectroscopy and Analysis Institute of Chemistry and Chemical Technology SB RAS Federal Research Center ‘Krasnoyarsk Science Center SB RAS' 50/24 Akademgorodok Krasnoyarsk 660036 Russian Federation

5. Department of Pharmacy with a PE-course Prof. V.F. Voino-Yasenetsky Krasnoyarsk State Medical University 1, Partizana Zheleznyaka str. Krasnoyarsk 660022 Russian Federation

Abstract

AbstractThe direct N‐alkylation reactions of ambident 3,5‐substituted 4‐nitroso‐1H‐pyrazoles are described for the first time. An efficient method of the 4‐nitroso‐1H‐pyrazoles and their sodium alkyl‐, allyl‐ salts regioselective N‐alkylation by benzyl halides, halocarboxylic acids esters, and related bifunctional alkylating agents is established with the use of superbasic conditions or reflux in acetone. A series of new N‐functionalized nitrosopyrazoles and bis(4‐nitrosopyrazole) compounds is successfully obtained with a yield of up to 85 %. Using quantum‐chemical calculations, it is shown that in terms of kinetics and thermodynamics, the N‐alkylation of the considered pyrazoles is a more advantageous process than O‐alkylation.

Publisher

Wiley

Subject

General Chemistry

Cited by 1 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Modification of N-Functionalized 4-Nitroso-1H-pyrazoles;Russian Journal of Organic Chemistry;2024-05

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