5813-88-7Relevant academic research and scientific papers
Selective C-N coupling reaction of diaryliodonium salts and dinucleophiles
Ma, Chang,Wu, Xufeng,Zeng, Qingle,Zhou, Lihong,Huang, Yi
, p. 2873 - 2877 (2017)
N-Aryl-α-amino amides including their chiral isomers have demonstrated important applications as pharmaceutical drugs; however, to date, a one-step synthetic route for them still remains to be developed. Herein, an efficient ligand-free copper-catalyzed selective C-N coupling reaction of diaryliodonium salts and dinucleophiles under mild conditions was realized. Diaryliodonium salts prefer to react with dinucleophiles at the site of stronger alkalic amino groups. Thus, a general aliphatic amino-selective N-arylation of α-amino amides was disclosed. Additionally, copper-catalyzed N-arylation of diaryliodonium salts afforded the same products as obtained via palladium-catalyzed reactions of aryl halides.
Synthesis of α-amino acid amides: Ruthenium-catalyzed amination of α-hydroxy amides
Zhang, Min,Imm, Sebastian,Baehn, Sebastian,Neumann, Helfried,Beller, Matthias
supporting information; experimental part, p. 11197 - 11201 (2012/02/03)
Give me an N: The catalytic amination of α-hydroxy amides with a variety of amines, including anilines, primary and secondary aliphatic amines, and ammonia, yields a wide range of α-amino amides (see scheme). This atom-efficient amination protocol proceeds efficiently in the presence of a commercially available [Ru3(CO)12]/DCPE catalyst system. Copyright
Electrophilic amination of 2-azadienes
Gouverneur,Ghosez
, p. 7585 - 7598 (2007/10/03)
2-Azadienes 1 bearing a trialkylsilyloxy group on position 3 can be regarded as carboxylic acid synthons. Their cycloadditions with several classes of nitroso compounds have been studied in detail as well as the transformation of the adducts into α-amino acids. The study showed that arylnitroso compounds such as nitrosobenzene reacted with 2-azadienes to give adducts that are potential precursors of α-N-arylamino acids. We have outlined an important limitation to the use of α-chloronitroso compounds. They are not compatible with highly functionalized dienes like 2-azadienes. On the other hand α-cyanonitroso and acylnitroso compounds reacted with azadienes to give adducts which were readily converted into α-amino acid derivatives.
