|
|
|
| Radical cation salts induced domino reaction of anilines with enol ethers:Synthesis of 1,2,3,4-tetrahydroquinoline derivatives |
| Xiao Dong Jiaa,b, Yan Rena, Cong Dde Huoa, Wen Juan Wanga, Xiang Ning Chena, Qiong Fua, Xi Cun Wanga |
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 |
|
|
|
|
Abstract 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.
|
|
Received: 30 September 2010
|
| Fund: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 |
|
Corresponding Authors:
Xiao Dong Jia, E-mail address:jiaxd1975@nwnu.edu.cn
E-mail: jiaxd1975@nwnu.edu.cn
|
|
|
|
| [1] |
Ming-Hua Chen, Sheng Lin, Ya-Nan Wang, Cheng-Gen Zhu, Yu-Huan Li, Jian-Dong Jiang, Jian-Gong Shi. Antiviral stereoisomers of 3,5-bis(2-hydroxybut-3-en-1-yl)-1,2, 4-thiadiazole from the roots of Isatis indigotica[J]. CCL, 2016, 27(05): 643-648. |
|
|
|
|
