1604839-65-7Relevant articles and documents
Copper-mediated C-H(sp2)/C-H(sp3) coupling of benzoic acid derivatives with ethyl cyanoacetate: An expedient route to an isoquinolinone scaffold
Zhu, Wei,Zhang, Dengyou,Yang, Nan,Liu, Hong
, p. 10634 - 10636 (2014)
A facile, copper-mediated, direct C-H(sp2)/C-H(sp3) bond coupling of benzoic acid derivatives with ethyl cyanoacetate by the deployment of an 8-aminoquinoline moiety as a bidentate directing group is disclosed. Such a unique transfor
Pd-Catalyzed Trifluoromethylthiolation of Unsaturated Compounds: A General Approach
Zhao, Qun,Chen, Mu-Yi,Poisson, Thomas,Pannecoucke, Xavier,Bouillon, Jean-Philippe,Besset, Tatiana
supporting information, p. 6167 - 6175 (2018/10/20)
In this study, a general approach towards the synthesis of trifluoromethylthiolated olefinic and aromatic compounds was developed. Under Pd-catalysis, the direct introduction of a SCF3 group was realized in the presence of the Munavalli reagent as the electrophilic SCF3 source and in the absence of additives. A large number of acrylamides and aromatic amides derived from 8-aminoquinoline and 5-methoxy-aminoquinoline were functionalized in moderate to high yields (up to 89 %). The cleavage of the directing groups was smoothly achieved, demonstrating further the synthetic utility of the present approach and offering a straightforward access to various original SCF3-containing molecules.
A First Example of Cobalt-Catalyzed Remote C H Functionalization of 8-Aminoquinolines Operating through a Single Electron Transfer Mechanism
Whiteoak, Christopher J.,Planas, Oriol,Company, Anna,Ribas, Xavi
supporting information, p. 1679 - 1688 (2016/10/13)
The development of new C H functionalization protocols based on inexpensive cobalt catalysts is currently attracting significant interest. Functionalized 8-aminoquinoline compounds are high-potential building blocks in organic chemistry and pharmaceutical compounds and new facile routes for their preparation would be highly valuable. Recently, copper has been applied as catalyst for the functionalization of 8-aminoquinoline compounds and found to operate through a single electron transfer (SET) mechanism, although requiring elevated reaction temperatures. Herein, we described the first example of a cobalt-catalyzed remote C H functionalization of 8-aminoquinoline compounds operating through a SET mechanism, exemplified using a practical and mild nitration protocol. The reaction uses inexpensive cobalt nitrate hexahydrate [Co(NO3)2?6 H2O] as catalyst and tert-butyl nitrite (TBN) as nitro source. This methodology offers the basis for the facile preparation of many new functionalized 8-aminoquinoline derivatives. (Figure presented.).
