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2005
Benzothiazole derivatives
R 0270
Synthesis of Benzothiazoles via ipso Substitution of ortho-Methoxythiobenz— The formation of benzothiazoles by cyclization of thiobenzamides bearing
10- 132 amides.
electron-donating methoxy groups on the primary ring is investigated. Jacobson cyclization of ortho-methoxythiobenzamides bearing one or two electron-donating
groups on the ring occurs with replacement of the ortho hydrogen, cf. formation of (II).
In the case of three electron-donating groups on the primary ring, however, cyclization
occurs in low yield, with ipso substitution of the ortho methoxy group, cf. formation of
(IV). The AIBN-induced cyclization of ortho-methoxythiobenzamides with two or
more electron-donating groups on the primary ring affords the corresponding benzothiazoles (VI) in high yields with ipso substitution of the ortho methoxy group. —
(DOWNER, N. K.; JACKSON*, Y. A.; Org. Biomol. Chem. 2 (2004) 20, 3039-3043;
Dep. Chem., Univ. West Indies, Mona, Kingston 7, West Indies, Jamaica; Eng.) —
Bartels
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