- Nucleophilic Displacements of Imidazoles.I. Oxygen,Nitrogen and Carbon Nucleophiles
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4(5)-Bromo- and -iodo-imidazoles, activated by an adjacent nitro substituent, undergo nucleophilic displacement with methoxide, phenoxide, cyclic secondary amines and cyanide.The regiochemistry of the reactions of 5-iodo-4-nitroimidazole with methoxide has been confirmed by spectroscopic and X-ray methods, and a number of erroneous structures from the literature have been revised.Some apparently anomalous reactions of methoxide with 5-halo-1,2-dimethyl-4-nitroimidazoles, and of cyanide with 4-halo-1-methyl-5-nitroimidazole have been noted.The crystal and molecular structure of 5-methoxy-1-methyl-4-nitroimidazole has been determined by direct methods.Crystals are monoclinic, P21/c, a 10.929(3), b 8.899(2), c 7.290(2) Angstroem; β 92.87(2) deg; Z 4.The structure was refined to R=0.095 for 818 reflections (I.2?I).
- Kulkarni, Surendra,Grimmett, M. Ross,Hanton, Lyall R.,Simpson, Jim
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p. 1399 - 1413
(2007/10/02)
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- REACTIONS OF 4,5-DINITROIMIDAZOLE AND 4(5)-NITROIMIDAZOLE-5(4)-SULFONIC ACID WITH NUCLEOPHILES
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The reactions of 4,5-dinitroimidazole and 5(4)-nitroimidazole-4(5)-sulfonic acid with nucleophilic agents were studied.Mercapto-, alkoxy-, and aminonitroimidazoles were synthesized.In the reaction of dinitroimidazole with sodium alkoxides 5(4)-nitroimidazole was obtained in addition to alkoxynitroimidazoles.It is shown that in the formation of salts of the starting imidazoles with bases nucleophilic-substitution reactions take place only with "soft" reagents.
- Mokrushin, V. S.,Belyaev, N. A.,Kolobov, M. Yu.,Fedotov, A. N.
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p. 650 - 652
(2007/10/02)
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