86918-13-0Relevant academic research and scientific papers
Chemoselective isocyanide insertion into the N-H bond using iodine-DMSO: Metal-free access to substituted ureas
Bora, Porag,Bez, Ghanashyam
supporting information, p. 8363 - 8366 (2018/08/03)
Insertion of isocyanides into the N-H bond gives access to many medicinally important and structurally diverse complex nitrogen-containing heterocycles. Although the transition metal catalyzed isocyanide insertion into the N-H bond is very common, polymerization of isocyanides in the presence of a transition metal and their strong coordination with metals are the common drawbacks. On the other hand, the inertness of most of the isocyanides towards amines in the absence of a metal catalyst has stymied the growth of the metal-free approach for isocyanide insertion into amines. As a result, only a handful of metal catalysed methods with limited substrate scopes have been reported for the synthesis of ureas via isocyanide insertion into amines and no metal-free version has been reported yet. Interestingly, chemoselective isocyanide insertion into amines has not been reported in the literature. We employed the I2-DMSO reagent system for the chemoselective synthesis of ureas, where isocyanides react with aliphatic amines only, while aromatic amines need a nucleophilic activator (DABCO) to facilitate the formation of ureas. This method gave direct and chemoselective access to ureas by evading the commonly used yet toxic isocyanates.
Amidomercuriation: A General Addition of Amides and Related Compounds to Olefins
Barluenga, Jose,Jimenez, Carmen,Najera, Carmen,Yus, Miguel
, p. 591 - 593 (2007/10/02)
The addition of different carboxamides and related compounds such as urethane or urea to olefins using mercury(II) nitrate followed by sodium borohydride reduction to give the corresponding N-substituted amides, urethanes, or ureas, respectively, is described.The monoalkylated ureas, through the same amidomercuriation-demercuriation procedure, yield symmetrical and unsymmetrical N,N'-disubstituted ureas.This amidomercuriation-demercuriation process provides a new, convenient, and general method for the Markovnikov amidation of carbon-carbon double bonds.
