54904-03-9Relevant academic research and scientific papers
Iridium(III)-Catalyzed Tandem Annulation of Pyridine-Substituted Anilines and α-Cl Ketones for Obtaining 2-Arylindoles
Cui, Xin-Feng,Qiao, Xin,Wang, He-Song,Huang, Guo-Sheng
, p. 13517 - 13528 (2020/12/15)
A facile and expeditious protocol for the synthesis of 2-arylindole compounds from readily available N-(2-pyridyl)anilines and commercially available α-Cl ketones through iridium-catalyzed C-H activation and cyclization is reported here. As a complementary approach to the conventional strategies for indole synthesis, the transformation exhibits powerful reactivity, tolerates a large number of functional groups, and proceeds with good to excellent yields under mild conditions, providing a straightforward method to obtain structurally diverse and valuable indole scaffolds. Furthermore, the reaction could be easily scaled up to gram scale.
Ruthenium-catalyzed synthesis of indole derivatives from: N -aryl-2-aminopyridines and alpha-carbonyl sulfoxonium ylides
Cui, Xin-Feng,Ban, Zi-Hui,Tian, Wa-Fa,Hu, Fang-Peng,Zhou, Xiao-Qiang,Ma, Hao-Jie,Zhan, Zhen-Zhen,Huang, Guo-Sheng
supporting information, p. 240 - 243 (2019/01/10)
Indole is a ubiquitous structural motif with important applications in many areas of chemistry. Given this, a simple and efficient Ru(ii)-catalyzed synthesis of indole via intermolecular annulation of N-aryl-2-aminopyridines and sulfoxonium ylides was proposed and accomplished. Excellent selectivity and good functional group tolerance of this transformation were observed. This protocol provides easy access to a wide variety of useful indoles in the presence of a commercially available [Ru(p-cymene)Cl2]2 catalyst. A possible mechanism for the reaction pathway was also proposed. More importantly, this reaction will offer a useful method for the construction of enantioenriched indole frameworks.
Inverting Conventional Chemoselectivity in Pd-Catalyzed Amine Arylations with Multiply Halogenated Pyridines
Keylor, Mitchell H.,Niemeyer, Zachary L.,Sigman, Matthew S.,Tan, Kian L.
supporting information, p. 10613 - 10616 (2017/08/15)
A new catalyst system capable of selective chloride functionalization in the Pd-catalyzed amination of 3,2- and 5,2- Br/Cl-pyridines is reported. A reaction optimization strategy employing ligand parametrization led to the identification of 1,1′-bis[bis(dimethylamino)phosphino]ferrocene "DMAPF", a readily available yet previously unutilized diphosphine, as a uniquely effective ligand for this transformation.
Reaction of Aromatic N-Oxides with Dipolarophiles. VII. Effect of Aromaticity on 1,3-Dipolar Cycloaddition Reactivity of Substituted Pyridine N-Oxides and Preparation of Oxazolopyridine Derivatives
Matsuoka, Toshikazu,Shinada, Minoru,Suematsu, Fumihiro,Harano, Kazunobu,Hisano, Takuzo
, p. 2077 - 2090 (2007/10/02)
The 1,3-dipolar cycloaddition reactivity of pyridine N-oxides to phenyl isocyanate was calculated by the MINDO/3 MO method using the perturbation equation derived by Klopman and Salem.The calculated did not predict the low reactivity of acceptor substitut
