V. Tkachuk, O. Hordiyenko, I. V. Omelchenko
Oct 20, 2018
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Journal
Monatshefte für Chemie - Chemical Monthly
Abstract
An efficient and simple synthetic protocol for the synthesis of a number methyl esters of 2-(N-hydroxycarbamimidoyl)benzoyl-substituted (S)-α-amino acids via subsequent coupling and hydroxyamination of 2-cyanobenzamide derivatives has been developed. Comparative analysis of three pseudopeptide series based on 2-cyano- and 2-amidoxime-substituted benzoic acid and its pyridine and pyrazine counterparts has been provided and it has revealed a practical advantage of the benzoic acid derivatives due to their greater availability. The impact of the nitrogen atom in the aromatic ring on the trans/cis-amide equilibrium in the proline derivatives is discussed.Graphical abstract