27463-92-9Relevant articles and documents
Intramolecular alkylations of aromatic compounds, XV: Synthesis of 4-methyl-5,6,7,8-tetrahydro-5-quinolinone
Reimann,Friesinger
, p. 871 - 878 (1985)
-
Highly efficient and enantioselective hydrogenation of quinolines and pyridines with Ir-Difluorphos catalyst
Tang, Weijun,Sun, Yawei,Lijin, Xu,Wang, Tianli,Qinghua Fan,Lam, Kim-Hung,Chan, Albert S.C.
supporting information; experimental part, p. 3464 - 3471 (2010/08/21)
The combination of the readily available chiral bisphosphine ligand Difluorphos with [Ir(COD)Cl]2 in THF resulted in a highly efficient catalyst system for asymmetric hydrogenation of quinolines at quite low catalyst loadings (0.05-0.002 mol%), affording the corresponding products with high enantioselectivities (up to 96%), excellent catalytic activities (TOF up to 3510 h-1) and productivities (TON up to 43000). The same catalyst was also successfully applied to the asymmetric hydrogenation of trisubstituted pyridines with nearly quantitative yields and up to 98% ee. In these two reactions, the addition of I2 additive is indispensable; but the amount of I2 has a different effect on catalytic performance. The Royal Society of Chemistry 2010.
Nitrogen fixation: Synthesis of heterocycles using molecular nitrogen as a nitrogen source
Mori, Miwako,Akashi, Masaya,Hori, Masanori,Hori, Katsutoshi,Nishida, Mayumi,Sato, Yoshihiro
, p. 1655 - 1670 (2007/10/03)
Nitrogen fixation using transition metals is a fascinating process. We have already reported on the incorporation of molecular nitrogen into organic compounds using a titanium-nitrogen complex reported by Yamamoto. We developed a novel titanium-catalyzed nitrogenation procedure using TiCl4 in the presence of an excess amount of Li and TMSCl. In this reaction, a 1 atm pressure of nitrogen gas can be used and the reaction proceeds at room temperature. The procedure is very simple. A THF solution of TiCl4 or Ti(O iPr)4 (1 equiv.), Li (10 equiv.), and TMSCl (10 equiv.) was stirred under an atmosphere of nitrogen at room temperature overnight to give titanium-nitrogen complexes. Although the structures of the titanium-nitrogen complexes have not yet been determined, they would consist of N(TMS)3, X2TiN(TMS)2, and XTi=NTMS. Using this procedure, various heterocycles, such as indole, quinoline, pyrrole, pyrrolizine, and indolizine derivatives, could be synthesized from molecular nitrogen in good-to-moderate yields as a stoichiometric reaction based on a titanium complex by a one-pot reaction. Furthermore, monomorine I and pumiliotoxin C were synthesized from molecular nitrogen as a nitrogen source. This procedure was further extended for the syntheses of heterocycles using a catalytic amount of titanium complex; also, indole and pyrrole derivatives were obtained in high yields.
