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.
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.
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.
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.
