M. Guetschow
Jun 15, 1999
Citations
0
Influential Citations
25
Citations
Journal
The Journal of organic chemistry
Abstract
The reaction of N-(mesyloxy)phthalimides with secondary amines was examined. Transformations are accomplished by one-pot reactions to optionally afford corresponding 2-ureidobenzamides, 2-ureidobenzoic acids, ethyl 2-ureidobenzoates, or isatoic anhydrides, respectively. The mechanism of the acid-catalyzed hydrolysis (or alcoholysis) of intermediate 2-ureidobenzamides to 2-ureidobenzoic acids (or esters) is discussed. A proton transfer mechanism involving the ureido moiety as an internal acid catalyst is proposed. Intermediate 2-ureidobenzoic acids undergo a further transformation to isatoic anhydrides. The utilization of the obtained 2-ureidobenzamides, 2-ureidobenzoic acids, and ethyl 2-ureidobenzoates to prepare 3,1-benzoxazin-4-ones is demonstrated.