Dehydrogenation of ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydrobenzofuran-2-carboxylate 1 with 2,2′-azobisisobutyronitrile and N-bromosuccinimide gave ethyl 4-hydroxy-3-methylbenzofuran-2-carboxylate 3. Reaction of compounds 3-4 with hydrazine hydrate afforded the corresponding hydrazides 5a-b. The reaction of 5a-b with aldehydes yielded substituted hydrazones 6a-l. Compounds 7a-d were prepared from compounds 6a-d and bromine in acetic acid. Lead tetraacetate oxidation of compounds 6e-l afforded substituted oxadiazoles 8e-l. Selenium dioxide oxidation of 4-oxo-4,5,6,7-tetrahydrobenzofuran semicarbazones 9, 14a and 4-oxo-4,5,6,7-tetrahydrobenzothiophene 14b gave the tricyclic 1,2,3-selenadiazoles 10, 15a and 15b respectively. Reaction of semicarbazones 9, 14a and 14b with thionyl chloride afforded the corresponding 1,2,3-thiadiazoles 12, 16a and 16b respectively.

Synthesis of [1,2,3]Selenadiazolo[4,5-e]benzofuran of Benzothiophene, [1,2,3]Thiadiazolo[4,5-e]benzofuran or Benzothiophene, and 2-Benzofuranyl-1,3,4-oxodiazoleDerivatives. -With regard to the potential biochemical and physiological activity of the title compounds, these structures are prepared as drugs against tropical diseases. Some unexpected compounds are obtained prepared according to literature methods. Thus, attempted cyclization of (V) with both bromine and lead tetraacetate fails. Also, reaction of (XIIa) with thionyl chloride does not give the 4,5-dihydrobenzofuran derivative but the oxidized benzofuran derivative (XIV). -(SHEKARCHI, M.; ELLAHIYAN, F.; AKBARZADEH, T.; SHAFIEE*, A.; J. Heterocycl. Chem. 40 (2003) 3, 427-433; Dep. Chem., Fac. Pharm., Tehran Univ., Tehran, Iran; Eng.) -H. Hoennerscheid 43-091