Chemistry of Heterocyclic Compounds

, Volume 45, Issue 3, pp 327–335 | Cite as

Synthesis of 2,4-diphenyl-1H-pyrrol-1-amine derivatives

  • L. M. PotikhaEmail author
  • V. A. Kovtunenko
  • A. V. Turov
  • G. V. Palamarchuk
  • R. I. Zubatyuk
  • O. V. Shishkin

The direction of the reaction of 4-bromo-1,3-diphenyl-2-buten-1-one (γ-bromodypnone) with hydrazines depends on the nature of the substituent they contain. Reaction with 1-methylhydrazinium hydrosulfate gives 1-methyl-3,5-diphenylpyridazin-1-ium bromide but carboxylic acid hydrazides give N-(2,4-diphenyl-1H-pyrrol-1-yl)carboxylic acid amides. γ-Bromodypnone and phenylhydrazine give both 1,3,5-triphenyl-1,4-dihydropyridazine and N,2,4-triphenyl-1H-pyrrol-1-amine (15%). 1-(2,4-Dinitrophenyl)hydrazine gives the 2,4-dinitrophenylhydrazone of (Z)-4-bromo-1,3-diphenyl-2-buten-1-one. Condensation of 2,4-diphenyl-1H-pyrrol-1-amine with aromatic aldehydes readily leads to N-(arylmethylidene)-2,4-diphenyl-1H-pyrrol-1-amines and alkylation with methyl iodide gives N,N-dimethyl-2,4-diphenyl-1H-pyrrol-1-amine.


1-aminopyrrole γ-bromodypnone 2,4-diphenyl-1H-pyrrol-1-amine 3,5-diphenylpyri-dazine 


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Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • L. M. Potikha
    • 1
    Email author
  • V. A. Kovtunenko
    • 1
  • A. V. Turov
    • 1
  • G. V. Palamarchuk
    • 2
  • R. I. Zubatyuk
    • 2
  • O. V. Shishkin
    • 2
  1. 1.Taras Shevchenko National UniversityKievUkraine
  2. 2.Institute for Single CrystalsUkraine National Academy of SciencesKharkivUkraine

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