868565-59-7Relevant 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
, p. 2614 - 2621 (2021)
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.
Oxamyl dipeptide caspase inhibitors developed for the treatment of stroke
Linton, Steven D.,Aja, Teresa,Allegrini, Peter R.,Deckwerth, Thomas L.,Diaz, Jose-Luis,Hengerer, Bastian,Herrmann, Julia,Jahangiri, Kathy G.,Kallen, Joerg,Karanewsky, Donald S.,Meduna, Steven P.,Nalley, Kip,Robinson, Edward D.,Roggo, Silvio,Rovelli, Giorgio,Sauter, Andre,Sayers, Robert O.,Schmitz, Albert,Smidt, Robert,Ternansky, Robert J.,Tomaselli, Kevin J.,Ullman, Brett R.,Wiessner, Christoph,Wu, Joe C.
, p. 2685 - 2691 (2007/10/03)
Structural modifications were made to a previously described acyl dipeptide caspase inhibitor, leading to the oxamyl dipeptide series. Subsequent SAR studies directed toward the warhead, P2, and P4 regions of this novel peptidomimetic are described herein.