A general synthesis of symmetrically disubstituted ureas and trisubstituted ureas by direct Pdcatalyzed oxidative carbonylation of primary amines or of a mixture of a primary and a secondary amine, respectively, with unprecedented catalytic efficiencies for this kind of process, is reported. Reactions are carried out at 90-100 °C in DME as the solvent in the presence of PdI2 in conjunction with an excess of KI as the catalytic system and under 20 atm of a 4:1 mixture of CO and air. In some cases, working in the presence of an excess of CO2 (40 atm) in addition to CO and air (60 atm total) had a beneficial effect on substrate reactivity and product yield. Cyclic five-membered and six-membered ureas were easily formed from primary diamines. The methodology has been successfully applied to the synthesis of pharmacologically active ureas, such as those deriving from R-amino esters or urea NPY5RA-972, a potent antagonist of the neuropeptide Y5 receptor.

Efficient synthesis of ureas by direct palladium-catalyzed oxidative carbonylation of amines

GABRIELE, Bartolo;MANCUSO R.;
2004-01-01

Abstract

A general synthesis of symmetrically disubstituted ureas and trisubstituted ureas by direct Pdcatalyzed oxidative carbonylation of primary amines or of a mixture of a primary and a secondary amine, respectively, with unprecedented catalytic efficiencies for this kind of process, is reported. Reactions are carried out at 90-100 °C in DME as the solvent in the presence of PdI2 in conjunction with an excess of KI as the catalytic system and under 20 atm of a 4:1 mixture of CO and air. In some cases, working in the presence of an excess of CO2 (40 atm) in addition to CO and air (60 atm total) had a beneficial effect on substrate reactivity and product yield. Cyclic five-membered and six-membered ureas were easily formed from primary diamines. The methodology has been successfully applied to the synthesis of pharmacologically active ureas, such as those deriving from R-amino esters or urea NPY5RA-972, a potent antagonist of the neuropeptide Y5 receptor.
2004
Carbonylation; Palladium; Ureas
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11770/145834
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