Vilsmeier-Haack reagent: A facile synthesis of 2-(4-chloro-3,3-dimethyl-7-phenoxyindolin-2-ylidene)malonaldehyde and transformation into different heterocyclic compounds

Abstract

2-(5-Chloro-2-phenoxyphenyl)hydrazine was converted to corresponding 3H-indole by Fischer method utilizing the isopropyl methyl ketone in acetic acid. The reaction of 3H-indole with Vilsmeier-Haack reagent furnished aminomethylene malonaldehyde in excellent yield while the reactions of malonaldehyde with hydrazine, arylhydrazines, amines, cyanoacetamide and hydroxylamine hydrochloride, led to the corresponding pyrazole derivatives, enamines, cyanopyridone, and cyanoacetamide derivatives respectively.

Keywords

• Vilsmeier-Haack reagent
• Fischer indole synthesis malonaldehydes
• pyrazoles
• enamines
• cyanoacetamide
• cyanopyridone