Oxidant and Transition-Metal-Free Photoinduced Direct Oxidative Annulation of 1‑Aryl-2-(furan/thiophen-2-yl)butane-1,3-diones

A photoinduced direct oxidative annulation of 1-aryl-2-(furan/thiophen-2-yl)­butane-1,3-diones and ethyl-2-(furan-2-yl)-3-oxo-3-(aryl-2-yl)­propanoates in EtOH without the need for any transition metals and oxidants provided access to highly functionalized polyheterocyclic 1-(5-hydroxynaphtho­[2,1-b...

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Veröffentlicht in:Journal of organic chemistry 2017-12, Vol.82 (23), p.12097-12105
Hauptverfasser: Zhang, Jin, Zhang, Xi, Wang, Tao, Yao, Xinbo, Wang, Pei, Wang, Ping, Jing, Sisi, Liang, Yong, Zhang, Zunting
Format: Artikel
Sprache:eng
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Zusammenfassung:A photoinduced direct oxidative annulation of 1-aryl-2-(furan/thiophen-2-yl)­butane-1,3-diones and ethyl-2-(furan-2-yl)-3-oxo-3-(aryl-2-yl)­propanoates in EtOH without the need for any transition metals and oxidants provided access to highly functionalized polyheterocyclic 1-(5-hydroxynaphtho­[2,1-b]­furan-4-yl)­ethanones and 1-(5-hydroxyfuran/thieno/pyrrolo­[3,2-e]­benzofuran-4-yl)­ethanones. The phenomenon of excited-state intramolecular proton transfer (ESIPT) was observed for both 1-(5-hydroxynaphtho­[2,1-b]­furan-4-yl)­ethanone and 1-(5-hydroxy furan/thieno/pyrrolo­[3,2-e]­benzofuran-4-yl)­ethanone analogues.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b01839