The coupling reaction of 3-cyanoacetyl-2-methylindole 1a with the aromatic diazonium salts gave the corresponding arylhydrazones <b>2a-e</b>. Compounds <b>2</b> were used for synthesis of 4-aminopyrazole-5-carbonitrile <b>4a-e</b> and 5-amino-4-arylazo-3-pyrazoles <b>5a-e</b> derivatives. Also, treatment of 3-cyanoacetyl-2-phenylindole <b>1b</b> with phenyl isothiocyanate gave the corresponding thioacetanilide <b>7</b>. The later compound <b>7</b> was utilized as the key intermediate for the synthesis of some new thiadiazole derivatives <b>9a-r</b>. The structures of all new compounds were elucidated on the basis of elemental analysis and spectral data.
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