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.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 404–414, March, 2009.
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Potikha, L.M., Kovtunenko, V.A., Turov, A.V. et al. Synthesis of 2,4-diphenyl-1H-pyrrol-1-amine derivatives. Chem Heterocycl Comp 45, 327–335 (2009). https://doi.org/10.1007/s10593-009-0269-8
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DOI: https://doi.org/10.1007/s10593-009-0269-8