Catalytic oxidative carbonylation of diamines to cyclic ureas

I&EC 4

Lisa McElwee-White, lmwhite@chem.ufl.edu, Ampofo K. Darko, Seth Dumbris, and F. Chris Curran. Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, FL 32611-7200
Catalytic carbonylation provides an alternative to phosgene or phosgene derivatives such as 1,1-carbonyldiimidazole for the conversion of amines to ureas. Primary and secondary amines can be catalytically carbonylated to ureas using W(CO)6 as catalyst, I2 as the oxidant, and CO as the carbonyl source. Tolerance of a wide variety of functional groups makes this method suitable for highly functionalized substrates. This method has been used in the preparation of the core structure (1) and derivatives of the HIV protease inhibitors, DMP 323 and DMP 450. Other targets to be discussed include biotin (2) and hydantoin derivatives (3).

 

Alternative Resources for the Chemical Industry
8:30 AM-11:55 AM, Sunday, April 6, 2008 Morial Convention Center -- Rm. 223, Oral

Division of Industrial & Engineering Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008