164219-31-2Relevant articles and documents
Supporting-Electrolyte-Free Anodic Oxidation of Oxamic Acids into Isocyanates: An Expedient Way to Access Ureas, Carbamates, and Thiocarbamates
Petti, Alessia,Fagnan, Corentin,van Melis, Carlo G. W.,Tanbouza, Nour,Garcia, Anthony D.,Mastrodonato, Andrea,Leech, Matthew C.,Goodall, Iain C. A.,Dobbs, Adrian P.,Ollevier, Thierry,Lam, Kevin
supporting information, p. 2614 - 2621 (2021/06/27)
We report a new electrochemical supporting-electrolyte-free method for synthesizing ureas, carbamates, and thiocarbamates via the oxidation of oxamic acids. This simple, practical, and phosgene-free route includes the generation of an isocyanate intermediate in situ via anodic decarboxylation of an oxamic acid in the presence of an organic base, followed by the one-pot addition of suitable nucleophiles to afford the corresponding ureas, carbamates, and thiocarbamates. This procedure is applicable to different amines, alcohols, and thiols. Furthermore, when single-pass continuous electrochemical flow conditions were used and this reaction was run in a carbon graphite Cgr/Cgr flow cell, urea compounds could be obtained in high yields within a residence time of 6 min, unlocking access to substrates that were inaccessible under batch conditions while being easily scalable.
Syntheses of morpholine-2,3-diones and 2-hydroxymorpholin-3-ones: Intermediates in the synthesis of aprepitant
Nelson, Todd D.,Rosen, Jonathan D.,Brands, Karel M.J.,Craig, Bridgette,Huffman, Mark A.,McNamara, James M.
, p. 8917 - 8920 (2007/10/03)
The preparation of morpholine-2,3-diones and 2-hydroxymorpholin-3-ones from N-substituted β-amino alcohols is reported. These were useful intermediates in the synthesis and development of aprepitant.
The Use of Heterocycles for the Conformational Restriction of Biologically Active Peptoids
Horwell, David C.,Lewthwaite, Russell A.,Pritchard, Martyn C.,Ratcliffe, Giles S.,Rubin, J. Ronald
, p. 4591 - 4606 (2007/10/03)
A series of piperazinone ring systems have been synthesized as a means of evaluating the effect of conformational restriction of high affinity non-peptide NK1, NK3 and CCK-B receptor ligands.The synthesis of the targeted heterocycles is described along with a discussion of their affinities for their respective receptor types.