Functionalized Benzofurans via Microwave-Promoted Tandem Claisen-Rearrangement/5-endo-dig Cyclization
- Ortho-allyloxy alkinyl benzenes undergo, upon microwave irradiation in dimethylformamide, a tandem sequence of Claisen-rearrangement and 5-endo-dig cyclization to furnish 7-allyl-substituted benzofurans. With terminal alkynes, chroman-4-ones and enaminoketones become the main products. A mechanistic proposal for this observation relies on a reaction of the starting material with the solvent dimethylformamide under the microwave conditions.
| Author details: | Christiane SchultzeGND, Bernd SchmidtORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1002/jhet.3671 |
| ISSN: | 0022-152X |
| ISSN: | 1943-5193 |
| Title of parent work (English): | Journal of heterocyclic chemistry |
| Publisher: | Wiley |
| Place of publishing: | Hoboken |
| Publication type: | Article |
| Language: | English |
| Date of first publication: | 2019/08/18 |
| Publication year: | 2019 |
| Release date: | 2020/11/30 |
| Volume: | 56 |
| Issue: | 9 |
| Number of pages: | 11 |
| First page: | 2619 |
| Last Page: | 2629 |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Peer review: | Referiert |
