Oxidative photochemical cyclization of ethyl 3-(indol-3-yl)-3-oxo-2-phenylpropanoate derivatives: synthesis of benzo[a]carbazoles. Issue 21 (27th May 2015)

• Record Type: Journal Article
• Authors: Li, Yinlong; Pang, Zhonghua; Zhang, Tianqi; Yang, Jidong; Yu, Wei
• Is Part Of: Tetrahedron. Volume 71:Issue 21(2015)
• Page Start: 3351
• Page End: 3358
• Publication Date: 2015-05-27
• Subjects: Photocyclization -- Benzo[a]carbazole -- Ethyl 3-(1-methyl-1H-indol-3-yl)-3-oxopropanoates -- Ullmann–Hurtley reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.03.107
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 6-Ethoxycarbonyl-5-hydroxy-benzo[ a ]carbazoles were prepared from ethyl 3-(1-methyl-1 H -indol-3-yl)-3-oxopropanoates in two steps: the first step involved α-arylation of the indicated starting materials via Ullmann–Hurtley reaction; in the key second step, the thus formed coupling products underwent oxidative photocyclization to afford the benzo[ a ]carbazole ring. The present photocyclization features the use of CuBr2 to prompt the transformations, which could not be realized under the conventional conditions. Graphical abstract: