267666-10-4Relevant articles and documents
Synthesis of 1,2,4-trisubstituted-1,2,5,6-tetrahydropyridines
Chang, Meng-Yang,Lee, Ming-Fang,Lee, Nien-Chia,Huang, Yu-Ping,Lin, Chung-Han
, p. 588 - 591 (2011/03/18)
A novel method for the synthesis of 1,2,4-trisubstituted- or 1,2,3,4-tetrasubstituted-1,2,5,6-tetrahydropyridine is presented. The process was carried out by the bromomethoxylation of 4-substituted-1,2,5,6- tetrahydropyridines 1 with N-bromosuccinimide (NBS) in methanol, dehydrobromination with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and boron trifluoride etherate (BF3-OEt2)-catalyzed cross coupling of the corresponding enamine with trimethylsilyl-based nucleophiles. Homokainoid analogs were also synthesized via the protocol.
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.