Triflic Acid-Mediated Condensation of Phthalimide with Diaryl Ethers as a Route to Spiro-Isoindolinones: Mechanistic Insights and Related Reactions Научная публикация
| Журнал |
Journal of Organic Chemistry
ISSN: 0022-3263 , E-ISSN: 1520-6904 |
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| Вых. Данные | Год: 2024, Том: 89, Номер: 21, Страницы: 15931–15940 Страниц : 10 DOI: 10.1021/acs.joc.4c02139 | ||||
| Ключевые слова | PROTONATION; DEAROMATIZATION; DERIVATIVES | ||||
| Авторы |
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| Организации |
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Информация о финансировании (2)
| 1 | Министерство науки и высшего образования Российской Федерации (с 15 мая 2018) | FWUR-2024-0035 |
| 2 | Министерство науки и высшего образования Российской Федерации (с 15 мая 2018) | FWUE-2022-0012 |
Реферат:
Phthalimide and N-phenylphthalimide smoothly condense with di-p-tolyl ether in triflic acid (CF3SO3H, TfOH) to obtain the corresponding spiro[isoindoline-1,9′-xanthen]-3-ones. Structural analogs of phthalimide, such as phthalic anhydride and 1,3-indandione (but not saccharin), show similar reactivity. In contrast, N-(tetrafluoropyridin-4-yl)phthalimide reacts with DTE by an alternative pathway, yielding isobenzofuran dispiro derivative. The mechanistic aspects of these reactions are discussed on the basis of in situ NMR and theoretical (DFT) studies, providing insights on the key intermediacy of O,O-diprotonated forms of the starting compounds.
Библиографическая ссылка:
Genaev A.M.
, Salnikov G.E.
, Koltunov K.Y.
Triflic Acid-Mediated Condensation of Phthalimide with Diaryl Ethers as a Route to Spiro-Isoindolinones: Mechanistic Insights and Related Reactions
Journal of Organic Chemistry. 2024. V.89. N21. P.15931–15940. DOI: 10.1021/acs.joc.4c02139 WOS Scopus PMID OpenAlex
Triflic Acid-Mediated Condensation of Phthalimide with Diaryl Ethers as a Route to Spiro-Isoindolinones: Mechanistic Insights and Related Reactions
Journal of Organic Chemistry. 2024. V.89. N21. P.15931–15940. DOI: 10.1021/acs.joc.4c02139 WOS Scopus PMID OpenAlex
Даты:
| Поступила в редакцию: | 26 авг. 2024 г. |
| Принята к публикации: | 8 окт. 2024 г. |
| Опубликована online: | 15 окт. 2024 г. |
| Опубликована в печати: | 1 нояб. 2024 г. |
Идентификаторы БД:
| Web of science: | WOS:001333470400001 |
| Scopus: | 2-s2.0-85206542760 |
| PMID (PubMed): | 39404170 |
| OpenAlex: | W4403424636 |