Тип публикации: статья из журнала

Год издания: 2023

Идентификатор DOI: 10.1002/slct.202302031

Ключевые слова: nitrogen heterocycles, alkylation, nitroso compounds, Marcus theory, DFT calculations

Аннотация: The 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 estaПоказать полностьюblished 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.

Журнал: ChemistrySelect

Выпуск журнала: Т.8, №28

Номера страниц: 202302031

ISSN журнала: 23656549

Место издания: Вайнхайм

• Bobrova Anastasiia V. (Department of Organic Chemistry and Technology of Organic Substances, Reshetnev Siberian State University of Science and Technology)
• Krasnov Pavel O. (International Research Center of Spectroscopy and Quantum Chemistry, Siberian Federal University)
• Radzhabov Amirbek D. (Research School of Chemistry and Applied Biomedical Sciences, Tomsk Polytechnic University)
• Kondrasenko Alexander A. (Laboratory of Molecular Spectroscopy and Analysis, Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center ‘Krasnoyarsk Science Center SB RAS')
• Root Evgeniy V. (Department of Pharmacy with a PE-course, Prof. V.F. Voino-Yasenetsky Krasnoyarsk State Medical University)
• Suboch Georgii A. (Department of Organic Chemistry and Technology of Organic Substances, Reshetnev Siberian State University of Science and Technology)

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