Citation: Xiao Dong Jia, Yan Ren, Cong Dde Huo, Wen Juan Wang, Xiang Ning Chen, Qiong Fu, Xi Cun Wang. Radical cation salts induced domino reaction of anilines with enol ethers:Synthesis of 1,2,3,4-tetrahydroquinoline derivatives[J]. Chinese Chemical Letters, ;2011, 22(6): 671-674. doi: 10.1016/j.cclet.2010.12.038 shu

Radical cation salts induced domino reaction of anilines with enol ethers:Synthesis of 1,2,3,4-tetrahydroquinoline derivatives

a Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education, Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, China;
b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China

Received Date: 30 September 2010

Fund Project: We thank NSFC (No.21002079) and Project (No.20096203120002) supported by the Ministry of Education of the People's Republic of China.We also thank the third Knowledge and Technological Innovation Project(No.NWNUKJCXGC- 03-75 and NWNU-KJCXGC-03-64)of Northwest Normal University for supporting our research

A domino reaction of anilines with cyclic and acyclic enol ethers induced by catalytic amounts of TBPA^·+(5 mol%)was investigated and a series of 2,4-disubstituted-1,2,3,4-tetrahydroquinolines were synthesized.Different from cyclic enol ethers, when acyclic enol ethers were used in the reaction, they serve as surrogates of acetaldehyde, producing a series of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines.A single electron transfer mechanism was proposed to rationalize the products formation.
- Domino reaction,
- Radical cation salts,
- 1,2,3,4-Tetrahydroquinoline,
- Enol ether
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