open access

https://hdl.handle.net/2115/90362

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

英語

[2+2] Cycloaddition

2023-02

John Wiley & Sons

Journal of Heterocyclic Chemistry

60(2)

219-231

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.

学術雑誌論文

Accepted Manuscript

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.

0022-152X