30252-15-4Relevant articles and documents
Synthesis of α-Amidoketones through the Cascade Reaction of Carboxylic Acids with Vinyl Azides under Catalyst-Free Conditions
Gao, Cai,Zhou, Qianting,Yang, Li,Zhang, Xinying,Fan, Xuesen
, p. 13710 - 13720 (2020/11/13)
An efficient synthesis of α-amidoketone derivatives through the cascade reactions of carboxylic acids with vinyl azides is presented. Compared with literature protocols, notable features of this new method include catalyst-free conditions, broad substrate scope, good tolerance of a wide range of functional groups, and high efficiency. In addition, the synthetic potential of this method as a tool for late-stage modification was convincingly manifested by its application in the structural elaborations of a number of carboxylic acid drug molecules.
Photocatalytic Vicinal Aminopyridylation of Methyl Ketones by a Double Umpolung Strategy
Choi, Wonjun,Hong, Sungwoo,Im, Honggu
, p. 17511 - 17516 (2020/08/14)
A photocatalytic double umpolung strategy for the vicinal aminopyridylation of ketones was developed using pyridinium N?N ylides. The inversion of the polarity of the pyridinium N?N ylides by single-electron oxidation successfully enables radical-mediated 1,3-dipolar cycloadditions with enolsilanes formed in situ from ketones, followed by homolytic cleavage of the N?N bond. Intriguingly, the nucleophilic amino and electrophilic pyridyl groups in the ylides can be installed at the nucleophilic α-position and electrophilic carbonyl carbon, respectively, which are typically inaccessible by their innate polarity-driven reactivity. This method accommodates a broad scope, and the utility was further demonstrated by the late-stage functionalization of complex biorelevant molecules. Moreover, the strategy can be successfully applied to enamides.
