Nitroazoles: Synthesis, Structure and Applications

The crystal structure of 1-methyl-2,4-dinitro-5-iodoimidazole, C4H3IN4O4

“…Polynitroimidazole systems have been used as antifungal, antibacterial, antiviral, antitumor drugs and their intermediates [1][2][3]. Recently, these so called "high energy density materials" have attracted renewed attention in conjunction with their favorable detonation performance [4,5].…”

Crystal structure of 2,5-diiodo-4-nitro-1H-imidazole hemihydrate, C6H4I4N6O5

“…Polynitroimidazole systems have been used as antifungal, antibacterial, antiviral, antitumor drugs [1][2][3]. Recently, these so called "high energy density materials" have attracted renewed attention in conjunction with their favorable detonation performance [4,5].…”

1,4-Dinitro-1H-imidazoles

“…In contrast, 1,4-dinitro-1H-pyrazoles have recently been reviewed by Zaitsev et al 11 Some scattered information on dinitroimidazoles 1-5 can be found in the general review on nitroazoles published by Larina and Lopyrev. 12 Over a dozen years ago, two reviews briefly reported on cine and ANRORC reactions of 1,4-dinitro-1H-imidazoles with nucleophiles. 13,14 Compound 1 is a versatile reagent that can be applied not only to the preparation of dinitroimidazole 8, as was mentioned earlier, but it is also a starting material for convenient syntheses of 5(4)-alkoxy-4(5)-nitro-1H-imidazoles (11), 5(4)-amino-4(5)-nitro-1H-imidazoles (12), and particularly of 1-alkyl-4-nitro-1H-imidazoles (13) and 1-aryl-4-nitro-1H-imidazoles (14) (Figure 3).…”

“…48 The products served as starting materials in syntheses of adenines. Two other compounds, the (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) N)adenine and (1-3 H)ribose, were also prepared. The compounds were then enzymatically coupled to isotopically modified ribosyl groups to give respectively substituted adenosines (31, Figure 5).…”

“…N)imidazol-1′-yl]acetic acid was obtained. The latter acid with bromine and phosphorus trichloride in anhydrous benzene formed a product that was subjected to hydrolysis to afford 2-methyl-4(5)-nitro-1H- (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) N)imidazole in 40% yield. Starting compound 2 was also treated with ( 15 N)ammonia to produce a mixture of isotopically modified and natural nitrous oxide.…”