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The first examples of thiazolo[4,5-e]benzoisoxazoles are obtained from bromination of dihydrobenzo[d]isoxazol-4(5H)-one followed by cyclocondensation with thiourea, in the presence of DDQ. Analogously, cyclocondensation with thioamides provided 7,8-dihydrothiazolo[4,5-e]benzoisoxazoles. A 55-member library of these heterocycles is reported.

Synthesis of Thiazolo- and 7,8-Dihydrothiazolo[4,5-e]benzoisoxazoles