SYNTHESIS OF 2,4-DIPHENYL-1H-PYRROL-1-AMINE DERIVATIVES

Authors

  • Л. М. Потиха Taras Shevchenko National University, Kiev 01033
  • В. А. Ковтуненко Taras Shevchenko National University, Kiev 01033
  • А. В. Туров Taras Shevchenko National University, Kiev 01033
  • Г. В. Паламарчук Institute for Single Crystals, Ukraine National Academy of Sciences, Kharkiv 61001
  • Р. И. Зубатюк Institute for Single Crystals, Ukraine National Academy of Sciences, Kharkiv 61001
  • О. В. Шишкин Institute for Single Crystals, Ukraine National Academy of Sciences, Kharkiv 61001

DOI:

https://doi.org/10.1007/6777

Keywords:

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

Abstract

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.

How to Cite
Potikha, L. M.; Kovtunenko, V. A.; Turov, A. V.; Palamarchuk, G. V.; Zubatyuk, R. I.; Shishkin, O. V.  Chem. Heterocycl. Compd. 2009, 45, 327. [Khim. Geterotsikl. Soedin. 2009, 404.]

For this article in the English edition see DOI 10.1007/s10593-009-0269-8


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Published

2022-04-27

Issue

No. 3 (2009)

Section

Original Papers