Synthesis of 2,4-diphenyl-1H-pyrrol-1-amine derivatives |
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Authors: | L M Potikha V A Kovtunenko A V Turov G V Palamarchuk R I Zubatyuk O V Shishkin |
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Institution: | (1) Taras Shevchenko National University, Kiev, 01033, Ukraine;(2) Institute for Single Crystals, Ukraine National Academy of Sciences, Kharkiv, 61001, Ukraine |
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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.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 404–414, March, 2009. |
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Keywords: | 1-aminopyrrole γ -bromodypnone 2 4-diphenyl-1H-pyrrol-1-amine 3 5-diphenylpyri-dazine |
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