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Sequential Modification of Pyrrole Ring with up to Three Different Nucleophilesстатья
Статья опубликована в высокорейтинговом журнале
Статья опубликована в журнале из списка Web of Science и/или Scopus- Авторы: Shambalova Victoria E., Larkovich Roman V., Aldoshin Alexander S., Lyssenko Konstantin A., Nechaev Mikhail S., Nenajdenko Valentine G.
- Журнал: Journal of Organic Chemistry
- Год издания: 2024
- Издательство: American Chemical Society
- Местоположение издательства: United States
- DOI: 10.1021/acs.joc.4c00726
- Аннотация: An umpolung strategy was used for the preparation of highly functionalized 3-pyrrolin-2-ones. This approach involves dearomative double chlorination of 1H-pyrroles to form highly reactive dichloro-substituted 2H-pyrroles. The resulting intermediate reacts selectively with wet alcohols to form the corresponding alkoxy-substituted 3-pyrrolin-2-ones via double nucleophilic substitution in up to 99% yield. The subsequent reaction with different N-, O-, and S-nucleophiles opens access to highly functionalized pyrrolinones bearing additional functionality. The overall outcome of the reported sequence is step-by-step nucleophilic modification of pyrroles with three different nucleophiles. All steps were found to be highly efficient and 100% regioselective. This transformation proceeds under mild conditions and does not require any catalyst to give final products in very high yields. The obtained experimental results are in perfect agreement with the data obtained by theoretical investigation of these reactions.
- Добавил в систему: Алдошин Александр Сергеевич
Прикрепленные файлы
| № | Имя | Описание | Имя файла | Размер | Добавлен |
|---|---|---|---|---|---|
| 1. | Полный текст | JOC_2024_3-pyrrolin-2-ones.pdf | 2,2 МБ | 7 августа 2024 [alexander.aldoshin] | |
| 2. | Заключение-JOC-пирролиноны.jpeg | Заключение-JOC-пирролиноны.jpeg | 667,1 КБ | 6 сентября 2024 [alexander.aldoshin] |