6976-49-4Relevant academic research and scientific papers
Electrochemical anion pool synthesis of amides with concurrent benzyl ester synthesis
Mevan Dissanayake,Melville, Alex D.,Vannucci, Aaron K.
supporting information, p. 3165 - 3171 (2019/06/18)
An electrosynthesis method for amide bond formation has been developed in an attempt to increase the atom economy for this class of reactions. This "anion pool" method electrochemically generates strong nucleophiles from amine substrates. The amine nucleophiles then react with acid anhydrides to generate amides, and the by-product from this reaction undergoes further chemical transformations to generate pharmaceutically relevant benzoic esters. These one-pot reactions are operationally simple, are performed at room temperature, and avoid rare transition metals and added bases. The amide synthesis is amenable to primary and secondary amines and a variety of anhydrides with yields up to 90% obtained. Atom economy and process mass index (PMI) values calculated for this procedure indicate that this process can be considered greener compared to traditional amide synthesis routes used by industry. Furthermore, this electrochemical approach showed unique selectivity when substrates that contained two inequivalent amine moieties were examined.
Novel Synthesis of Carbamic Ester from Carbon Dioxide, Amine, and Ortho Ester
Ishii, Shideru,Nakayama, Hidenobu,Yoshida, Yasuhiko,Yamashita, Tadataka
, p. 455 - 458 (2007/10/02)
Carbon dioxide reacted with aliphatic amines and ortho esters to form carbamic esters in good yields.The influence of different ortho esters on the carbamate synthetic reaction is described.In the case of orthocarbonates, carbamic esters were obtained in high yields.The reaction of carbon dioxide, amines, and ortho esters may involve a competitive reaction between the esterification of carbamic acid produced by a reaction of carbon dioxide with amine, and the alkylation of amine.
