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N-chloromethyl-2-thiono-benzoxazole 1 and benzothiazole 2 undergo nucleophilic substitution by sulfur, oxygen and nitrogen nucleophiles. Condensation of compounds land 2 with hydrazine, phenylhydrazine and hydroxylamine afforded the s-triazolo- and 1,2,4-oxadiazolo fused systems 13–18, respectively. The structures of the resulting products are assigned on the basis of spectral data and elemental analyses.
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