- Synthesis of 2,3-dihydro-7-nitroimidazo[5,1-b]oxazoles as potential tuberculostatic agents
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A series of 2,3-dihydro-7-nitroimidazo[5,1-b]oxazoles has been prepared in one-pot reaction. The proposed new method of their synthesis requires a treatment of 4,5-dinitroimidazole or 2-methyl-4,5-dinitroimidazole with oxiranes. Some of the obtained compounds have been tested in vitro for antimycobacterial activity and the spatial structure of them has been also discussed.
- Zwawiak, Justyna,Olender, Dorota,Zwolska, Zofia,Augustynowicz-Kopec, Ewa,Zaprutko, Lucjusz
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scheme or table
p. 229 - 233
(2009/04/04)
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- 1,4-Dinitroimidazole and Derivatives. Structure and Thermal Rearrangement
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Nitration of 4-nitroimidazole in acetic anhydride/glacial acetic acid gives 1,4-dinitroimidazole.The crystal and molecular structure of this compound have been determined by direct methods.Crystals are orthorombic; P212121, a 5.853(3), b 9.591(8), c 10.392(5) Angstroem, V 583.4(7) Angstroem3, Dm 1.76 g cm-1, Dc 1.80 g cm-1 (Z = 4); λ 0.71069 Angstroem; T 173 K.The structure was refined to R = 0.048 for 926 reflections 2?(I)>.Both 2-methyl-2-nitro- and 5-methyl-4-nitroimidazoles N-nitrate under the same conditions.When heated in solution at 100 -140 deg C 1,4-dinitro- and 2-methyl-1,4-dinitro-imidazoles rearrange to give C-nitro isomers and some denitration products, but 5(4)-methyl-1,4(5)-dinitroimidazole failed to give identifiable products.
- Grimmett, M. Ross,Hua, Sio-Tiok,Chang, Kuei-Choo,Foley, Sandra A.,Simpson, Jim
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p. 1281 - 1289
(2007/10/02)
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- Azoles. 27. Nitroimidazole derivatives, their antibacterial and fungicidal activity and electron affinity
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Nitroimidazole derivatives 3a-3g, 4a-4g and 5-8 were synthesized by treating 4,5-dinitro- and 2-methyl-4,5-dinitroimidazole (1,2) with phenacyl bromide, its p-substituted derivatives or epichlorohydrin. 1-(3-Chloro-2-hydroxypropyl)-4,5-dinitroimidazole (5) and its 2-methyl derivative 6 have been converted to imidazo-oxazoles 7 and 8 or amino imidazole derivatives 9-14 by the action of potassium carbonate or cyclic amines (pyrrolidine, piperidine, morpholine and N-methylpiperazine). Some of the newly synthesized nitroimidazole derivatives show antibacterial and fungicidal activity. The electron affinity of the nitroimidazole derivatives 1-24 is discussed on the basis of their half-wave potentials and in the connection with their eventual radiosensitizing properties.
- Zaprutko,Gajdzinski,Michalska,Pietkiewicz,Lutomski,Lukaszewski,Wrzeciono
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p. 817 - 820
(2007/10/02)
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