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A practical amine-free synthesis of symmetric ureas and thioureas by self-condensation if iso(thio)cyanates

Authordc.contributor.authorJiménez Blanco, José L. 
Authordc.contributor.authorSaitz Barría, Claudio es_CL
Authordc.contributor.authorBenito, Juan M. es_CL
Authordc.contributor.authorOrtíz Mellet, Carmen es_CL
Authordc.contributor.authorFuentes, José es_CL
Authordc.contributor.authorSantoyo González, Francisco es_CL
Authordc.contributor.authorGarcía Fernández, José M. es_CL
Cita de ítemdc.identifier.citationSynthesis Nº 11: 1907-1914es_CL
Abstractdc.description.abstractIsocianates and isothiocyanates are readily transformed into the corresponding symmetric N,N'-disubstituted ureas and thioureas upon treatment with pyridine-water with no formation of side products. Evidence is shown for an amine-free mechanistic pathway, probably involving (thio)carbamic anhydrides as reaction intermediates. The methodology is compatible with in situ generation of the isocyanate precursor from and acyl azide via Curtius rearrangement and with the presence of ester and amide functional groups in the molecule. Examples given include alkyl, aryl and carbohydrate substrates. This procedure allows the high yielding preparation of (thio)ureas in those cases where the related amine is not accessible.es_CL
Publisherdc.publisherThieme Stuttgartes_CL
Títulodc.titleA practical amine-free synthesis of symmetric ureas and thioureas by self-condensation if iso(thio)cyanateses_CL
Document typedc.typeArtículo de revistaes_CL

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