Ring opening of N-hydroxyphthalimide to construct phenylurea derivatives

Abstract

Arylurea and their analogues have been one of the most ubiquitous backbone during the past century, and extensive studies have been conducted to establish practical synthetic methods for their derivatives. In particular, it is an effective pathway to synthesize arylureas by using commercially available phthalimide compounds. Reported herein is a triethoxyphosphine promoted ring-opening of the N-hydroxyphthalimide (NHPI) by the nucleophilic attack of amines. This transformation shows a wide range of functional-group tolerance under mild reaction conditions.

Graphical Abstract

Keywords:

• N-hydroxyphthalimide
• phenylurea
• ring-opening reaction
• construction of C–N bond

Additional information

Funding

The present research was financially supported by Natural Science Foundation of Jiangsu Province [BK20161328].