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Synthesis of Benzothiazoles and Benzoxazoles from Thiobenzamides
N. K. Downer-Riley, Y. A. Jackson*
University of the West Indies, Kingston 7, Jamaica
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.