Reactivity of 3-Cyanoacetylindole Derivatives: Synthesis of 3-Hydrazonopyrazolyl and 3-Thiadiazolyl Indole Derivatives

Citation:
Hassaneen, H. M., and H. H. Z. A. M. E. Gomaa, "Reactivity of 3-Cyanoacetylindole Derivatives: Synthesis of 3-Hydrazonopyrazolyl and 3-Thiadiazolyl Indole Derivatives", International Journal of Organic Chemistry, 2011.

Abstract:

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

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