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

Hamdi M. Hassaneen, Huwaida M. E. Hassaneen, Zakaria Ahmed Gomaa

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DOI: 10.4236/ijoc.2011.13015                

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.

Keywords

3-Methyl Indole, 3-Phenyl Indole, Phenyl Isothiocyanate, Cyanoacetic Acid

Conflicts of Interest

The authors declare no conflicts of interest.

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