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.
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.
Zhang
Jianheng
J
Department of Chemistry, Tulane University, New Orleans, LA 70118, USA.
Li
Chao-Jun
CJ
D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D004988:Ethers, Cyclic / Q000737:chemistry*; D007204:Indium / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D014867:Water / Q000737:chemistry
D000814:Aniline Compounds; D004988:Ethers, Cyclic; D011804:Quinolines; D007204:Indium; D014867:Water; C020758:indium trichloride