Efficient and selective deprotection method for N-protected 2(3H)-benzoxazolones and 2(3H)-benzothiazolones

Tetradron 60 (2004) 10321-10324
Pascal Carato, Saïd Yousa, Didier Sellier, Jacques H. Poupaert, Nicolas Lebegue and Pascal Berthelot

Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, EA 1043, 3, rue du Professeur Laguesse, BP 83, 59006 Lille cedex, France
Laboratory of Medicinal Chemistry, School of Pharmacy, UCL, Avenue Emmanuel Mounier, 73, B-1200 Brussels, Belgium

Received 25 May 2004;  accepted 19 August 2004.  Available online 22 September 2004.


Abstract
Cyclic carbamate flanked with heterocyclic or aliphatic moieties are frequently used in medicinal chemistry. The synthesis of derivatives bearing a free NH often requires the use of a protection method. A literature search reveals very few protection/deprotection methods for cyclic carbamates. In this paper, we described different methods applicable to 2(3H)-benzoxazolone and 2(3H)-benzothiazolone.


Keywords: 2(3H)-Benzoxazolone; 2(3H)-Benzothiazolone; Protecting groups