Some reactions with ω-bromoacetophenone: Synthesis of Δαβ-butenolide and its transformation into pyrrole derivatives†

doi:10.1002/HC.520060116

Paper

Some reactions with ω-bromoacetophenone: Synthesis of Δαβ-butenolide and its transformation into pyrrole derivatives†

Published 1995 · F. M. Abdelrazek, Z. E. Kandeel, A. M. Salah

Heteroatom Chemistry

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10

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0

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Abstract

ω-Bromoacetophenone reacts with the sodium salt of ethyl cyanoacetate to afford α-cyano-β-phenyl-Δαβ-butenolide. This butenolide undergoes azo coupling with diazotized aromatic amines (ArNH2) to afford the hydrazo derivatives. These hydrazo derivatives (ArPh, 4-ClC6H4, 4-MeC6H4, 4-MeOC6H4) were transformed into the corresponding 3(2H)-pyridazinone derivatives on stirring in methanol in the presence of potassium hydroxide. These latter compounds were converted into the corresponding 3-cyano-2,5-dihydroxy-4-phenyl-N-arylpyrrole derivatives on reduction with zinc dust in refluxing acetic acid, presumably via reductive cleavage of the NN bond of the pyridazine followed by recyclization via loss of ammonia.

Study Snapshot

-Bromoacetophenone can be used to synthesize -butenolide and its transformation into pyrrole derivatives, with potential applications in organic synthesis and catalysis.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Some reactions with ω-bromoacetophenone: Synthesis of Δαβ-butenolide and its transformation into pyrrole derivatives†

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References

Heterocyclic Synthesis with Nitriles: Synthesis of Some New Mercapto-Substituted Heterocycles from Alkylidenemalononitrile

Mercapto-substituted heterocycles can be synthesized from alkylidenemalononitrile by azo coupling with aromatic amines, resulting in azo derivatives and pyrrole derivatives.

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