|
Hokkaido University Collection of Scholarly and Academic Papers >
Graduate School of Engineering / Faculty of Engineering >
Peer-reviewed Journal Articles, etc >
Formation of anti-Bredt-type azabicyclo[4.2.0]octene frameworks through photochemical intramolecular [2+2] cycloaddition between indole and a distal double bond of allene
| Title: | Formation of anti-Bredt-type azabicyclo[4.2.0]octene frameworks through photochemical intramolecular [2+2] cycloaddition between indole and a distal double bond of allene |
| Authors: | Arai, Noriyoshi Browse this author →KAKEN DB |
| Keywords: | Photochemistry | | Indole | | Indoline | | Allene | | [2+2] Cycloaddition |
| Issue Date: | Feb-2023 |
| Publisher: | John Wiley & Sons |
| Journal Title: | Journal of Heterocyclic Chemistry |
| Volume: | 60 |
| Issue: | 2 |
| Start Page: | 219 |
| End Page: | 231 |
| Publisher DOI: | 10.1002/jhet.4574 |
| Abstract: | Irradiation of 1-(penta-3,4-dienoyl)indole derivatives in the presence of an aromatic ketone by a high-pressure mercury lamp through Pyrex glass gave two types of cyclized products stereoselectively in high combined yields. The major product was a tetracyclic indoline derivative containing anti-Bredt-type azabicyclo[4.2.0]octene moiety produced via photo [2+2] cycloaddition between indole and a distal double bond of allene, accompanied by a small amount of proximal [2+2] adduct. Among a range of aromatic ketones screened, 3 ',4 '-methylenedioxyacetophenone was found to sensitize the substrate most effectively. |
| Rights: | This is the peer reviewed version of the following article: Arai, N., J. Heterocycl. Chem. 2023, 60(2), 219, which has been published in final form at https://doi.org/10.1002/jhet.4574. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/90362 |
| Appears in Collections: | 工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
|
Submitter: 新井 則義
|
