Synthesis of o-Nitroarylamines via Ipso Nucleophilic Substitution of Sulfonic Acids
A mild, efficient, and eco-friendly method for the synthesis of o-nitroarylamine from o-nitroaryl sulfonic acid via ipso nucleophilic aryl substitution by amine is described. The products have been obtained with good yields at room temperature without the assistance of any metal, activating agent, or toxic oxidant. This method is useful for racemization-free synthesis of N-aryl amino acid esters.
Iron- or Zinc-Mediated Synthetic Approach to Enantiopure Dihydroquinoxalinones
A general and efficient synthesis of enantiopure dihydroquinoxalinones has been developed using naturally occurring amino acids as starting materials. The reductive cyclization of N-(o-nitroaryl)amino esters was performed by using iron and zinc metal under mild conditions in a water/ethyl acetate mixture. The corresponding dihydroquinoxalinones were obtained in moderate to high yields and high enantiomeric purity, among which 7 new compounds were unprecedented in the literature.
Li, Dazhi,Ollevier, Thierry
supporting information
p. 1273 - 1280
(2019/01/04)
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