InCl(3)-catalyzed domino reaction of aromatic amines with cyclic enol ethers in water: a highly efficient synthesis of new 1,2,3,4-tetrahydroquinoline derivatives |
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Authors: | Zhang Jianheng Li Chao-Jun |
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Institution: | Department of Chemistry, Tulane University, New Orleans, LA 70118, USA. |
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Abstract: | The tetrahydroquinoline moiety is a structural feature of many natural products. By using a domino reaction of aromatic amines and cyclic enol ethers or 2-hydroxy cyclic ether catalyzed by indium chloride in water, various tetrahydroquinoline derivatives were synthesized efficiently. Most cyclization products showed cis selectivity. The use of 2,3-dihydrofuran as the cyclic enol ether provided both higher reactivity and cis selectivity than the use of 3,4-dihydro-2H-pyran. The cis selectivity was tentatively rationalized due to chelation control in water. |
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