Parallel synthesis of ureas and carbamates from amines and CO2 under mild conditions.
A mild and efficient library synthesis technique has been developed for the synthesis of ureas and carbamates from carbamic acids derived from the DBU-catalyzed reaction of amines and gaseous carbon dioxide. Carbamic acids derived from primary amines reacted with Mitsunobu reagents to generate isocyanates in situ which were condensed with primary and secondary amines to afford the desired ureas. Similarly, carbamic acids from secondary amines reacted with alcohols activated with Mitsunobu reagents to form carbamates.
Peterson
Scott L
SL
Department of Chemistry, Merck Research Laboratories, 33 Avenue Louis Pasteur, Boston, Massachusetts 02115, USA. scott_peterson@merck.com
Stucka
Sabrina M
SM
Dinsmore
Christopher J
CJ
D000588:Amines / Q000737:chemistry*; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D002245:Carbon Dioxide / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D014508:Urea / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
D000588:Amines; D002219:Carbamates; D002245:Carbon Dioxide; D014508:Urea