Synthese von 3‐[4‐Nitroimidazolyl‐(5)]‐1,2,4‐oxadiazolen

Simon, Helmut; Lettau, Herbert; Schubert, Hermann; Jumar, Alfred

doi:10.1002/zfch.19690090206

Cited by 4 publications

(1 citation statement)

References 6 publications

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“…The reaction of 5-halo-4-nitroimidazoles 13 with potassium or sodium cyanide in lower alcohols in the presence of the iodides of these metals as catalysts leads to high yields of 5-cyano-4-nitroimidazoles 68 [12,18,19,22,26,43,[70][71][72][73][74][75][76]. In DMSO this reaction takes place in the absence of the catalyst [12,73].…”

Section: Reactions With C-nucleophilesmentioning

confidence: 96%

Reactions of halonitroimidazoles with nucleophiles (review)

Александрова¹,

Кравченко

Кочергин³

2010

Chem Heterocycl Comp

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On account of their chemical stability, high reactivity, and availability 4(5)-halo-5(4)-nitro-and 2-halo-4(5)-nitroimidazoles have proved useful substrates for the study of reactions with O-, S-, N-, C-, and N,O-nucleophiles. The high reactivity of the halogen atom in the series of 4(5)-halo-5(4)-nitroimidazoles is brought about by the presence of the strong electron-accepting NO 2 group at the "ortho" position. The activating effect of the NO 2 group also extends to the halogen atom at position 2 of the imidazole ring.The products from the reactions of halonitroimidazoles with various nucleophiles have found use in fine organic synthesis, especially in the synthesis of heterocycles with a bridging nitrogen atom, biologically active compounds, and medicinal preparation. Thus, 1-methyl-4-nitro-5-(6-purinyl)mercaptoimidazole has found use under the name azathioprine as a medical preparations in the transplantation of vital organs and the treatment of a series of autoimmune diseases [1][2][3][4].

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