29314-09-8Relevant academic research and scientific papers
Highly Enantioselective Direct Synthesis of Endocyclic Vicinal Diamines through Chiral Ru(diamine)-Catalyzed Hydrogenation of 2,2′-Bisquinoline Derivatives
Ma, Wenpeng,Zhang, Jianwei,Xu, Cong,Chen, Fei,He, Yan-Mei,Fan, Qing-Hua
, p. 12891 - 12894 (2016)
An asymmetric hydrogenation of 2,2′-bisquinoline and bisquinoxaline derivatives, catalyzed by chiral cationic ruthenium diamine complexes, was developed. A broad range of chiral endocyclic vicinal diamines were obtained in high yields with excellent diastereo- and enantioselectivity (up to 93:7 dl/meso and >99 % ee). These chiral diamines could be easily transformed into a new class of chiral N-heterocyclic carbenes (NHCs), which are important but difficult to access.
Enantioselective Synthesis of 4-Cyanotetrahydroquinolines via Ni-Catalyzed Hydrocyanation of 1,2-Dihydroquinolines
Fang, Xianjie,Gao, Jihui,Jiao, Mingdong
supporting information, (2020/11/18)
A Ni-catalyzed asymmetric hydrocyanation that enables the formation of 4-cyanotetrahydroquinolines in good yields with excellent enantioselectivities is presented herein. A variety of functional groups are well-tolerated, and a gram-scale reaction supports the synthetic potential of the transformation. Additionally, several crucial intermediates for pharmaceutically active agents, including a PGD2 receptor antagonist, are now accessible through asymmetric synthesis using this new protocol.
Chemoselective One-Pot Synthesis of Functionalized Amino-azaheterocycles Enabled by COware
Clohessy, Thomas A.,Roberts, Alastair,Manas, Eric S.,Patel, Vipulkumar K.,Anderson, Niall A.,Watson, Allan J. B.
supporting information, p. 6368 - 6371 (2017/12/08)
Functionalized bicyclic amino-azaheterocycles are rapidly accessed in a one-pot cross-coupling/reduction sequence enabled by the use of COware. Incompatible reagents are physically separated in a single reaction vessel to effect two chemoselective transformations - Suzuki-Miyaura cross-coupling and heteroarene reduction. The developed method allows access to novel heterocyclic templates, including semisaturated Hedgehog and dual PI3K/mTOR inhibitors, which show enhanced physicochemical properties compared to their unsaturated counterparts.
METHOD OF PREPARING SILYLATIVE-REDUCED N-HETEROCYCLIC COMPOUND USING ORGANOBORON CATALYST
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Paragraph 245; 246; 247; 248, (2016/06/06)
Provided is a method of preparing a silylative-reduced N-heterocyclic compound by reducing an N-heteraromatic compound including a sp2 hybridized nitrogen atom while simultaneously introducing a silyl group into a beta-position with respect to a nitrogen atom of the N-heteroaromatic compound, using a silane compound, in the presence of an organoboron catalyst.
Synthesis and utility of dihydropyridine boronic esters
Panda, Santanu,Coffin, Aaron,Nguyen, Q. Nhu,Tantillo, Dean J.,Ready, Joseph M.
supporting information, p. 2205 - 2209 (2016/02/18)
When activated by an acylating agent, pyridine boronic esters react with organometallic reagents to form a dihydropyridine boronic ester. This intermediate allows access to a number of valuable substituted pyridine, dihydropyridine, and piperidine products.
Boron-catalyzed silylative reduction of quinolines: Selective sp3 C-Si bond formation
Gandhamsetty, Narasimhulu,Joung, Seewon,Park, Sung-Woo,Park, Sehoon,Chang, Sukbok
supporting information, p. 16780 - 16783 (2015/01/09)
A silylative reduction of quinolines to synthetically versatile tetrahydroquinoline molecules involving the formation of a C(sp3)-Si bond exclusively β to nitrogen is described. Triarylborane is a highly efficient catalyst (up to 1000 turnovers), and silanes serve as both a silyl source and a reducing reagent. The present procedure is convenient to perform even on a large scale with excellent stereoselectivity. Mechanistic studies revealed that the formation of a 1,4-addition adduct is rate-limiting while the subsequent C(sp3)-Si bond-forming step from the 1,4-adduct is facile.
7-Chloroquinoline: a versatile intermediate for the synthesis of 7-substituted quinolines
Hirner, Joshua J.,Zacuto, Michael J.
scheme or table, p. 4989 - 4993 (2009/12/01)
A practical synthesis of 7-mono-substituted quinolines has been achieved. Selective reduction of the inexpensive commercial reagent 4,7-dichloroquinoline affords 7-chloroquinoline, which has been converted into more complex 7-mono-substituted quinolines through a series of Pd-catalyzed cross coupling reactions. These studies include the first examples of Suzuki reactions for the preparation of 7-mono-substituted quinolines as well as the first application of the Sonagashira reaction for the synthesis of 7-substituted quinolines. This strategy has been extended to the preparation of 2,7-di-substituted quinolines.
