Seyoung Jung, Seulgi Kim, Gee-Hyung Lee
Dec 20, 2012
Citations
0
Influential Citations
6
Citations
Journal
Bulletin of The Korean Chemical Society
Abstract
An efficient solid-phase methodology has been developed for the synthesis of 2-amino and 2-amidobenzo[d]oxazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo[d]oxazole resins 4 by cyclization reaction of 2-hydroxyphenylthiourea resin 3. The resin-bound 2-hydroxyphenylthiourea 3 is produced by the addition of 2-aminophenol to the isothiocyanate-terminated resin 2 and serve as a key intermediate for the linker resin. This core skeleton 2-aminobenzo[d]oxazole resin 4 undergoes functionalization reaction with various electrophiles, such as alkylhalides and acid chlorides to generate 2amino and 2-amidobenzo[d]oxazole resins 5 and 6 respectively. Finally, 2-amino and 2-amidobenzo[d]oxazole derivatives 7 and 8 are then generated in good yields and purities by cleavage of the respective resins 5 and 6 under trifluoroacetic acid (TFA) in dichloromethane (CH2Cl2).