1- Phenyl-2-methyl-4-nitroimidazole

Whereas several l-aryl-4-nitroimidazoles are found to be good sensitizers for superoxide ion formations85 (Type I photooxidation), only l-phenyl-2-methyl-4-nitroimidazole 140 is a photosensitizer for singlet oxygen, i.e. by energy transfer of type II photooxidation (equation 70). 

There has been some interest in the chemistry of aminonitroazoles when used as high energetic compounds. Data concerning direct introduction of the amino group into the nitroazole cycle have been absent in the literature till the present time. We have studied the vicarious nucleophilic substitution of l-methyl-4-nitropyrazole and also l-mcthyl-4-nitroimidazole (Table 3.10), 4-nitro-2-phenyl-1,2,3-triazole (Table 3.24), and nitrobenzimidazoles (Table 3.25) under the effect of 1,1,1-trim-ethylhydrazinium halides and 4-amino-1,2,4-triazole by NMR spectroscopy (DMSO-<76) (Scheme 3.5) [220, 272-278] ... 

The mass spectrum of I-methyl-4-nitroimidazole-5-carboxylic acid amide shows the elimination of water by an electron impact as distinct from the usual thermal process. In l,4,5-trimethylimidazole-2-carboxylic acid the principal loss is that of CO2. Subsequent loss of O, OH, and HCN was also observed (Schofield et al., p. 173). Ferguson and Schofield (pp. 172,173) have reported considerable data for imidazole JV-oxides. Thus 1-methoxy-4,5-dimethyl-2-phenylimidazole (which loses OCH3 and CH3CN from the fragment m/e 171) is readily distinguished from l,4,5-trimethyl-2-phenyl-imidazole 3-oxide (loss of O and OH). The spectra of 1-benzylimidazoles are dominated by the tropylium ion. ... 

Introduction of arylsulfonylmethyl substituents into nitroheteroaromatic rings is of great practical value because these sulfones are versatile intermediates in organic synthesis. Nitrobenzyl aryl sulfones and their heterocyclic analogues can easily be transformed into the corresponding ethenyl derivatives by a simple alkylation with simultaneous elimination of arylsulfinate anion [125]. Diethyl methylenemalonate substituent can be introduced in the positimi 4- of 5-nitroimidazole via the VNS reaction of 5-nitroimidazole with the carbanion of chloromethyl phenyl sulfone [112, 124], followed by condensation of the obtained 4-(phenylsulfonyl)methyl derivative with diethyl bromomalonate or diethyl ketomalonate (Scheme 33) [126]. 

Allopurinol (ethyl ethoxymethylene cyanoacetate), 0.01% pet Azathioprine (5-chloro-l-methyl-4-nitroimidazole), 0.01% pet Bumetanide (sulfonyl benzoic acids), 1% pet Chlorodiazepoxide (2-chloromethyl-4-phenyl-6-chlorquinazoline-3-oxide), 1% pet (44 controls neg) Chloroquine (4,7-dichloroquinoline), 5% pet Clenbuterol (4-amino-(x-bromo-3,5-dichloroacetophenone), 0.5% pet... 

A mixture of l,5-dimethyl-2-nitroimidazole and benzaldehyde in ethanolic KOH stirred 22.5 hrs. at room temp, under Ng l-methyl-2-nitro- -phenyl-5-imidazole-ethanol (Y 59%) added at room temp, to a stirred mixture of coned. H2SO4 and acetic acid, heated 20 min. at 110 in an oil bath l-methyl-2-nitro-5-styryl-imidazole (Y 86%). - This 2-stage process gives a better yield than direct condensation to the styryl deriv. G. Asato and G. Berkelhammer, J. Med. Chem. 15,1086 (1972). 

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