Triflic Acid-Mediated Condensation of Phthalimide with Diaryl Ethers as a Route to Spiro-Isoindolinones: Mechanistic Insights and Related Reactions Full article
| Journal |
Journal of Organic Chemistry
ISSN: 0022-3263 , E-ISSN: 1520-6904 |
||||
|---|---|---|---|---|---|
| Output data | Year: 2024, Volume: 89, Number: 21, Pages: 15931–15940 Pages count : 10 DOI: 10.1021/acs.joc.4c02139 | ||||
| Tags | PROTONATION; DEAROMATIZATION; DERIVATIVES | ||||
| Authors |
|
||||
| Affiliations |
|
Funding (2)
| 1 | Ministry of Science and Higher Education of the Russian Federation | FWUR-2024-0035 |
| 2 | Ministry of Science and Higher Education of the Russian Federation | FWUE-2022-0012 |
Abstract:
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.
Cite:
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
Dates:
| Submitted: | Aug 26, 2024 |
| Accepted: | Oct 8, 2024 |
| Published online: | Oct 15, 2024 |
| Published print: | Nov 1, 2024 |
Identifiers:
| Web of science: | WOS:001333470400001 |
| Scopus: | 2-s2.0-85206542760 |
| PMID: | 39404170 |
| OpenAlex: | W4403424636 |