38313-19-8Relevant articles and documents
Electronic Activity Tuning of Acyclic Guanidines for Lactide Polymerization
Eisenreich, Fabian,Viehmann, Philipp,Müller, Fabian,Hecht, Stefan
, p. 8729 - 8732 (2015)
Novel aromatic guanidine-based organocatalysts for the ring-opening of l-lactide were synthesized and applied in comprehensive polymerization experiments and kinetic studies. The introduction of electronically active substituents led to a significant chan
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.
Super fast cobalt carbonyl-mediated synthesis of ureas
Enquist, Per-Anders,Nilsson, Peter,Edin, Johan,Larhed, Mats
, p. 3335 - 3339 (2007/10/03)
Fast cobalt carbonyl-mediated generation of ureas from primary amines was performed using high-density microwave irradiation. This enhanced method permitted the preparation of symmetrical ureas in good yields and unsymmetrical ureas in moderate yields. Th