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Porównanie zachowania się 1,4-dinitroimidazoli i 1,4-dinitropirazoli wobec reagentów z ugrupowaniami NH2 lub NH

Jędrysiak R., Sawicki M., Suwiński J.

Chemik

2005

Vol. 58, nr 6

327-329

Niektóre nitroazole znajdują zastosowanie w medycynie i weterynarii. W pracy przedstawiono i porównano regioselektywne syntezy pochodnych 4-nitroimidazoli i 4-nitropirazoli w reakcjach anrorc lub podstawienia cine odpowiednich 1,4-dinitroazoli z reagentami zawierającymi ugrupowania NH2 lub NH.

Some nitroazoles have found applications in medicine or veterinary. In this work, we present and compare regioselective syntheses of 4-nitroimida-zole and 4-nitropyrazole derivatives in anrorc or cine substitution reactions of respective 1,4-dinitroazoles with reagents containing NH2 or NH groups.

Cine-Substitution of Nitro Group in 1-Aryl-2-methyl-4-nitroimidazoles by Thiols; X-ray Diffraction Proof for the Product Structure

Suwiński J., Świerczek K., Wagner P., Kubicki M., Borowiak T.

Polish Journal of Chemistry

2001

Vol. 75, nr 5

639-647

1-Aryl-2-methyl-4-nitroimidazoles react with 2-amino- or with 2-hydroxyethanethiols to give products of cine-substitution of the nitro group. 5-(2_-Hydroxyethylthio)-2- methyl-1-phenylimidazole has been isolated as a free base, other products in the form of dipicrates. A structure of 5-(2_-aminoethylthio)-2-methyl-1-phenylimidazole dipicrate was proved by X-ray diffraction.

Cine-Substitution of 2-Methyl-1,4-dinitroimidazole in Dimethylsulfoxide Solution. Synthesis of 4(5)-(Azol-1'-yl)-2-methyl-5(4)-nitroimidazoles

Walczak K., K. Świerczek K., Suwiński J.

Polish Journal of Chemistry

2001

Vol. 75, nr 5

673-676

4(5)-(Azol-1-yl)-5(4)-nitroimidazoles were obtained in moderate yields by nucleophilic cine-substitution of 2-methyl-1,4-dinitroimidazole. Nucleophilic azole anions were generated from salts of parent heterocycles with 1,8-diazabicyclo[5.4.0]-undec-7-ene.

Cine substitution in reaction of unactivated 2-halopyridines with 2-aminopyridine 1-oxide. Formation of 3-(2-pyridylamino)-2(1H)-pyridone [1]

Rykowski A., Pucko W.

Polish Journal of Chemistry

1998

Vol. 72, nr 11

2378-2383

Reaction of 2-aminopyridine 1-oxide 1a with 2-fluoropyridine 5a in DMF at 140 degree C gave 2-(2-pyridylamino)pyridine 1-oxide 6 (41%) along with bis(2-pyridyl)amine 7 (5%). However, heating in melt of 1a with 2-chloropyridine 5b or 2-bromopyridine 5c in the presence of dry potassium carbonate at 175 degree C provided 3-(2-pyridylamino)-2(1H)-pyridone 9 as cine substitution product. Compound 9 results from the nucleophilic attack of the N-oxide on the carbon atom bearing halogen to give corresponding cation 17, which rearranges to cine substitution product 9 via anhydro-base 18.