Synfacts 2007(12): 1246-1246  
DOI: 10.1055/s-2007-991408
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Benzothiazoles and Benzoxazoles from Thiobenzamides

Contributor(s): Victor Snieckus, Wei Gan
N. K. Downer-Riley, Y. A. Jackson*
University of the West Indies, Kingston 7, Jamaica
Further Information

Publication History

Publication Date:
22 November 2007 (online)


An iodine-initiated synthesis of benz­oxazoles and benzothiazoles from thiobenz­amides is reported. Electrophilic substitution mechanisms, initiated by S-iodination, are proposed to rationalize the reaction routes. Interestingly, the bulky isopropyl group and the electron-withdrawing tosyl group do not prevent the ortho oxygen from attacking the sulfenyl iodide; however, the yields are comparatively low and the scope requires more exploration.