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[3 + 2]-Cycloaddition of in Situ Generated Nitrile Imines and Acetylene for Assembling of 1,3-Disubstituted Pyrazoles with Quantitative Deuterium Labelingстатья
Статья опубликована в высокорейтинговом журнале
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 9 апреля 2021 г.
- Авторы: Voronin Vladimir V., Ledovskaya Maria S., Gordeev Evgeniy G., Rodygin Konstantin S., Ananikov Valentine P.
- Журнал: Journal of Organic Chemistry
- Том: 83
- Номер: 7
- Год издания: 2018
- Издательство: American Chemical Society
- Местоположение издательства: United States
- Первая страница: 3819
- Последняя страница: 3828
- DOI: 10.1021/acs.joc.8b00155
- Аннотация: A novel synthetic methodology for the preparation of 1,3-disubstituted pyrazoles from in situ generated nitrile imines and acetylene is reported. The reactions are performed in a simple two-chamber reactor. One part of the reactor is loaded with hydrazonoyl chloride precursors of active nitrile imine species and a base. The other part is used to generate acetylene from CaC2 and water. Partitioning of the reactants improves the yields of desired pyrazoles up to 99% and simplifies their isolation to a simple procedure of solvent evaporation. The approach requires no complex equipment and utilizes inexpensive, safe, and easy to handle calcium carbide as a starting material. A model deuterium incorporation is carried out according to the developed methodology, producing a series of novel 4,5-dideuteropyrazoles with excellent deuterium enrichment. Theoretical calculations on reaction mechanism and characterization of possible intermediate structures were performed.
- Добавил в систему: Анаников Валентин Павлович