64217-85-2Relevant academic research and scientific papers
Pd-catalysed oxidative carbonylation of amino alcohols to N,N′-bis(hydroxyalkyl)ureas under mild conditions using molecular oxygen as the oxidant
Giannoccaro, Potenzo,Ferragina, Carla,Gargano, Michele,Quaranta, Eugenio
, p. 78 - 84 (2010)
A very simple method has been developed for the selective synthesis of symmetrical N,N′-bis(hydroxyalkyl)ureas, OC[NH-(CH2)x-OH]2 (x = 3-6), by oxidative carbonylation of α,ω-amino alcohols [3-aminopropanol (3-AP), 4-aminobutanol (4-AB), 5-aminopentanol (5-APe), 6-aminohexanol (6-AH)] with CO/O2 mixtures (O2 = 5 mol%) in the presence of Pd(II)/ligand/NEt3·HI catalytic systems. The catalytic process takes place under very mild conditions (p(CO/O2) = 0.1 MPa; 303-333 K). The target products can be isolated in high yield through a very simple and straightforward procedure. The catalytic system can be easily recovered and recycled for several times. The influence of a few reaction parameters (nature of ancillary ligand and iodide co-catalyst, I/Pd molar ratio, etc.) on the catalytic activity has also been investigated and the main mechanistic features of the catalytic process fully elucidated.
A NEW SYNTHESIS OF HETEROCYCLES VIA CARBONILATION OF AMINES WITH CARBON MONOXIDE IN THE PRESENCE OF SELENIUM
Yoshida, Tohru,Kambe, Nobuaki,Ogawa, Akiya,Sonoda, Noboru
, p. 137 - 148 (2007/10/02)
Amines which contain a second functional group in the appropriate position react with carbon monoxide in the presence of selenium to form heterocyclic derivatives in which carbon monoxide is incorporated.For instance, diamines, aminoalcohols, and their related compounds undergo carbonylation to give cyclic ureas, urethanes and the corresponding carbonylated compounds.For diamines and amino alcohols with more than two carbon atoms between the functional groups, intermolecular carbonylative coupling takes place competing with the intramolecular reaction.High selectivity has been attained under specified reaction conditions.Anilines having cyano or acetyl groups on the ortho position afford new classes of selenium-containing heterocycles.In these reactions, carbamoselenoate has been suggested as the common key intermediate.
