196883-02-0Relevant articles and documents
Lewis acid-directed reactions of benzoquinone mono-/bis-imines: Application to syntheses of substituted β- and γ-tetrahydrocarbolines
Engler, Thomas A.,Wanner, Jutta
, p. 6135 - 6138 (1997)
Ti(IV)-promoted reactions of N-phenylsulfonyl-3- and 4-piperidone enol ethers with 2-alkoxy-4-(N-phenylsulfonyl)imino- 1,4-benzoquinone afford 8-alkoxy-7-hydroxy-tetrahydrocarbolines. However, reactions promoted by BF3 produce substituted benzo
Lewis Acid-Directed Cyclocondensation of Piperidone Enol Ethers with 2-Methoxy-4-(N-phenylsulfonyl)-1,4-benzoquinoneimine: A New Regioselective Synthesis of Oxygenated Carbolines
Engler, Thomas A.,Wanner, Jutta
, p. 2444 - 2457 (2007/10/03)
Lewis acid-directed cyclocondensations of piperidone enol ethers with 2-methoxy-4-(N-phenylsulfonyl)-1,4-henzoquinoneimine are reported. Benzofurans are obtained with BF3·OEt2 as a promoter, whereas use of excess amounts of TiCl4:Ti(OiPr)4 leads to tetrahydrocarbolines. The latter reactions provide expedient routes to oxygen-substituted tetrahydrocarbolines and carbolines. As applications of this new methodology, the preparations of 1-[3-(dimethylamino)propyl]amino-7-methoxy- and 1-[3-(dimethylamino)propyl]amino-7,8-dimethoxy-5H-pyrido[4,3-b]indoles are described.