Dihydrooxazole ring opening reactions in bicyclic nitroimidazodihydrooxazoles with simultaneous Williamson ethe real groups formation are described. It was found that only mutual action of K2CO3, phenol and alcohol can cause such reaction. Its mechanism consists of three steps. In a result, a series of 3-phenoxy-1-(5-alkoxy-4-ni tro- 1H-imidazol-1-yl)propan-2-ols has been obtained. The structure of new compounds was confirmed by single crystal X-ray analysis.
Several 1-(chloro, fluoro, dichloro or difluorophenyl)-4-nitroimidazoles and their 2-methyl derivatives have been prepared by the reaction of respectively substituted anilines with 1,4-dinitroimidazoles via a degenerated imidazole ring transformation. The structures of the obtained products were characterized by spectros copy and/or by X-ray analysis. Most of the products have been tested as My cobacterium tuberculosis inhibitors.
The title compounds have been obtained in reaction of 1,4-dinitroimidazoles with 2-amino-1,3-propanedioles in water-methanol solution. 1-(1,3-Dihydroxy-2-propyl)- 4-nitroimidazoles were transformed into derivatives that can be used for combinatorial oligomer synthesis.
Reaction of D-ribopyranosylamine or 2,3-O-isopropylidene-D-ribofuranosylamine with1,4-dinitroimidazoles in aqueous methanol affords appropriate4-nitroimidazole nucleoside derivatives.
Reaction of 4(5)-bromo-2-methyl-5(4)-nitroimidazole with phenacyl bromide derivatives gave two isomers: 4-bromo-5-niroimidazoles (4a-e) and 5-bromo-4-nitroimidazoles (5a-e). Compounds 5a-e were treated with cyclic secondary amines to afford expected 5-amino-4-nitroimidazole derivatives 6a-c - 10a-b.
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