20948-73-6Relevant articles and documents
Base-catalyzed aryl halide isomerization enables the 4-selective substitution of 3-bromopyridines
Bandar, Jeffrey S.,Puleo, Thomas R.
, p. 10517 - 10522 (2020/10/18)
The base-catalyzed isomerization of simple aryl halides is presented and utilized to achieve the 4-selective etherification, hydroxylation and amination of 3-bromopyridines. Mechanistic studies support isomerization of 3-bromopyridines to 4-bromopyridines proceedsviapyridyne intermediates and that 4-substitution selectivity is driven by a facile aromatic substitution reaction. Useful features of a tandem aryl halide isomerization/selective interception approach to aromatic functionalization are demonstrated. Example benefits include the use of readily available and stable 3-bromopyridines in place of less available and stable 4-halogenated congeners and the ability to converge mixtures of 3- and 5-bromopyridines to a single 4-substituted product.
Anticancer-Active N-Heteroaryl Amines Syntheses: Nucleophilic Amination of N-Heteroaryl Alkyl Ethers with Amines
Wang, Xia,Yang, Qiu-Xia,Long, Cheng-Yu,Tan, Yan,Qu, Yi-Xin,Su, Min-Hui,Huang, Si-Jie,Tan, Weihong,Wang, Xue-Qiang
supporting information, p. 5111 - 5115 (2019/07/03)
A mild amination protocol of N-heteroaryl alkyl ethers with various amines is described. This transformation is achieved by utilizing simple and readily available base as promoter via C-O bond cleavage, offering a new amination strategy to access several anticancer-active compounds. This work is highlighted by the excellent functional group compatibility, scalability, wide substrate scope, and easy derivatization of a variety of drugs.
