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

Jin Zhang; Xi Zhang; Tao Wang; Xinbo Yao; Pei Wang; Ping Wang; Sisi Jing; Yong Liang; Zunting Zhang

doi:10.1021/acs.joc.7b01839

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

J Org Chem. 2017 Dec 1;82(23):12097-12105. doi: 10.1021/acs.joc.7b01839. Epub 2017 Nov 2.

Authors

Jin Zhang¹, Xi Zhang¹, Tao Wang¹, Xinbo Yao¹, Pei Wang¹, Ping Wang¹, Sisi Jing¹, Yong Liang¹, Zunting Zhang¹

Affiliation

¹ Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China, and School of Chemistry and Chemical Engineering, Shaanxi Normal University , Xi'an 710119, People's Republic of China.

PMID: 29065264
DOI: 10.1021/acs.joc.7b01839

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't