Abstract

Article history: Received June 25, 2012 Received in Revised form November 5, 2012 Accepted 5 November 2012 Available online 5 November 2012 1-(2,5-Dichlorophenyl)hydrazine was converted via Fischer synthesis with isopropylmethylketone into 4,7-dichloro-2,3,3-trimethyl-3H-indole. Exposure of the indolenine to the vilsmeier reagent produced amino methylene malondialdehyde which reacted with hydrazine, arylhydrazine, urea, cyanoacetamide and thiourea to give pyrazols, pyrimidones and thiopyrimidone, respectively. © 2013 Growing Science Ltd. All rights reserved.

Highlights

  • The recognition of the power of the species produced by the combination of phosphoryl chloride with the amide of secondary amine (N-methylformanilide and dimethylformamide have been most often utilized) has its origin in paper in 18941

  • Baradarani and coworkers described the reaction of various 3H-indols with the Vilsmeier reagent formed from dimethyl formamide and phosphorus oxychloride to produce aminomethylene malondialdehyde[14,15,16,17]

  • Indolenine was reacted with the Vilsmeier reagent to produce aminomethylene malondialdehyde 3

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Summary

Introduction

The recognition of the power of the species produced by the combination of phosphoryl chloride with the amide of secondary amine (N-methylformanilide and dimethylformamide have been most often utilized) has its origin in paper in 18941. Later work by Fischer, Muller and Vilsmeier[2] and by Vilsmeier and Haack[3] and later by groups of Arnold[4,5,6], Meth-Cohn[7,8,9] and Perumal[10,11,12,13] clarified the process and made it into a widely used regimen of acylation, especially formylation of reactive aromatic and heteroaromatic compounds and non-aromatic compounds. The reaction of aminomethylene malondialdehyde with various aryl hydrazines led to form pyrazole ring on 3H-indole systems[14,15,16,17]

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