3158-26-7Relevant 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
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.
METHOD FOR PRODUCING ISOCYANATES
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Paragraph 0135; 0136, (2020/12/04)
The invention relates to a method for producing an isocyanate, wherein a carbamate or thiolcarbomate is converted, in the presence of a catalyst, with separation of an alcohol or thioalcohol, at a temperature of at least 150° C., to the corresponding isocyanate, wherein a compound of the general formula (X)(Y)(Z—H) is used as a catalyst, in particular characterized in that the compound has both a proton donor function and a proton acceptor function. In the catalysts according to the invention, a separable proton is bound to a heteroatom, which is more electronegative than carbon. Said heteroatom is either identical to Z or a component thereof. In the catalysts according to the invention, there is additionally a proton acceptor function which is either identical to X or a component thereof. According to the invention, the proton donator and proton acceptor function are connected to each other by the bridge Y.
N-Guanidino Derivatives of 1,5-Dideoxy-1,5-imino-d-xylitol are Potent, Selective, and Stable Inhibitors of β-Glucocerebrosidase
Sev?ek, Alen,?rot, Luka,Rihter, Jakob,?elan, Ma?a,van Ufford, Linda Quarles,Moret, Ed E.,Martin, Nathaniel I.,Pieters, Roland J.
, p. 483 - 486 (2017/04/10)
A series of lipidated guanidino and urea derivatives of 1,5-dideoxy-1,5-imino-d-xylitol were prepared from d-xylose using a concise synthetic protocol. Inhibition assays with a panel of glycosidases revealed that the guanidino analogues display potent inhibition against human recombinant β-glucocerebrosidase with IC50 values in the low nanomolar range. Related urea analogues of 1,5-dideoxy-1,5-imino-d-xylitol were also synthesized and evaluated in the same fashion and found to be selective for β-galactosidase from bovine liver. No inhibition of human recombinant β-glucocerebrosidase was observed for the urea analogues. Computational studies provided insight into the potent activity of analogues bearing the substituted guanidine moiety in the inhibition of lysosomal glucocerebrosidase (GBA).
