2-Methyl-6- imidazo

Using different mono- and diketones in acetic acid (at room temperature) afforded the following products from benzophenone, 2,2-diphenyl-2//-imid-azo[4,5-/]quinoline from dibenzylketone, the 2-benzyl-imidazo[4,5-/]quino-line and from 2,4-pentanedione, 2-methyl-imidazo[4,5-/]quinoline. Cyclohexanone under reflux gave 2-n-pentyl-, whereas at room temperature it afforded the. s pira[cyclohexane-l,2 ]-(2//)-imidazo[4,5-/]quinoline 108 (R R =(CFl2)5) (86UC527). 

Bromo-6-chloro-2-methyl-imidazo-( 1,2b)-pyridazine-bromine complex dichloromethane 20°C, 2 min. 75 % (40 %) (refs. 13,31)... 

Auch die Umsetzung von 1-substituierten 5-(Hydroximino-methyl)-imidazol-3-oxiden mit Es-sigsaureanhydrid zu 1-substituierten 2-Acetoxy-5-(hydroximino-methyl)-imidazo-len verlauft unter Wanderung der Acetoxy-Gruppe aus der 3- in die 2-Stellung72. 

Magee, J., Heat capacity and enthalpy of fusion for l-butyl-3-methyl-imidazo-lium hexafluoroplaosplaate. 17th lURAC Conference on Chemical Thermodynamics (ICCT 2002), Rostock, Germany, 2002. 

IQ 2-amino-3-methyl imidazo[4,5-/ quinoline nh2 r CH3 MelQx 2-amino-3,8-dimethyl imidazo [4,5-/ quinoxaline nh2 MelQ 2-amino-3,4-dimethyl imidazolOS quinoline nh2 W XH3... 

A nitro group at C-4 of methylated imidazo[4,5-c]pyridin-2(3H)-ones (157) can also be displaced by nucleophilic attack, by halide ions (74KGS854) or alkoxide ions giving (158), as well as being reduced to the amine (78MI41005). 

Yl. Yamazoe, Y., Shimada, M., Kamataki, T., et al.. Microsomal activation of 2-amino-3-methyl imidazo[4,5-/]quinoline, a pyrolysate of sardine and beef extracts, to a mutagenic intermediate. Cancer Res. 43, 5763-5774 (1983). 

Hasaniya, N., Youn, K., Xu, M., Hernaez, J., and Dashwood, R. 1997. Inhibitory activity of green and black tea in a free radical-generating system using 2-amino-3-methyl-imidazo[4,5-f]quinoline as substrate. Jpn. J. Cancer Res. 88 553-58. 

Three heterocyclic aromatic amines, 2-amino-3-methyl-imidazo[4, 5-f]quinoline (IQ),2-amino-3,4-dimethylimidazo[4,5-f]quinoxaline and 2-amino-3,4-dimethylimidazo[4,5-f]quinoline, have been found in boiled pork juice [109]. Six organosulfur compoimds - diallyl disulfide (DAD), dipropyl disulfide (DPD), diallyl sulftde (DAS), allyl methyl sulfide (AMS), allyl mercaptan (AM) and cysteine - were added separately to the pork juice before reflux boiling and then the mutagenicity of each sample was examined with the Salmonella typhimurium strain TA98 in the presence of S9 mix. All six compounds were found to inhibit the mutagenicity of boiled pork juice. The greatest inhibitory effect was observed with DAD and DPD, and this was 111-fold higher than that of... 

Triaza-compounds. Triazolium ylides (714) yield the 1,3-dipolar cyclo-adducts (715 R = C02Me or CN) with methyl acrylate or acrylonitrile. 6-Methyl-imidazo[l,2-Z>]pyrazole (716) is methylated at N-5 but acetylated at N-1. ... 

Knoevenagel condensation reactions of aldehydes with 2-imino-l-methyl-imidazo-lidine-4-one occurs rapidly under solvent-free reaction conditions at 160-170°C using a focused MW oven (Scheme 2.2-13) [49]. 

Heating 3,4-diaminopyridine with chloroacetic add gives 6-aza-2-quinazolone (IX-217), However, if glycollic acid or acetic anhydride is used instead of chloroacetic acid, 2-hydroxymethylimidazo [4,5-c] pyridine and 2-methyl-imidazo[4,5-c] pyridine are obtained, respectively. ... 

Mitsui T, Kimoto M, Harada Y, Sato A, Kitamura A, To T, Hirao 1, Yokoyama S (2002) Enzymatic incorporation of an unnatural base pair between 4-propynyl-pyrrole-2-carbaldehyde and 9-methyl-imidazo [(4,5)-b]pyridine into nucleic acids. Nucleic Acids Res Suppl 2 219-220... 

Ionic liquids (IL) can be used as solvents for nucleophilic substitution reactions of alkyl halides or tosylates with NaN3. ° The authors studied three ionic liquids (84 and 85), [bmim][PF6], [bmim][N(Tf)2]> [hpyr][N(Tf)2] (where bmim = l-butyl-3-methyl-imidazo-lium, hpyr = 1-hexylpyridinium, PFg = hexafluorophosphate, N(Tf)2 = bis(trifluoromethy lsulfonyl)imide). It was observed that nucleofugacity scales for this reaction are similar to those reported for the same process in cyclohexane. It was also observed that elimination reaction does not compete with substitution even in cases with sterically hindered substrates such as the triflate ester of diacetone-D-glucose 81. The nucleophilic displacement on n-octyl mesylate (86) with potassium azide in a biphase system of supercritical carbon dioxide (SCCO2) and water, in the presence of catalyst Bu4PBr is also an adequate medium for the synthesis of the corresponding azide 87 ° (Scheme 3.11). 

Bielectrophiles have found appreciable applications in the synthesis of ring-fused systems, especially those involving [5,6] fused systems. The following serve to illustrate these applications. Reaction of pyrazole with (chlorocarbonyl)phenyl ketene (214) (Type 1, Scheme 6) readily formed the zwitterionic pyrazolo[l,2-a]pyrazole derivative (215) (80JA3971). With l-methylimidazole-2-thione (216), anhydro-2-hydroxy-8-methyl-4-oxo-3-phenyl-4//-imidazo[2,l-6][l,3]thiazinium hydroxide (217) was obtained (80JOC2474). 

Imidazo[2,l-c][l,2,4]dithiazole-3-thione HNMR,6, 904 <71TL1317> 4/7-Imidazol-5-amine, 4-cyano-4-methyl- H NMR, 5, 16 <83UP40100>... 

Imidazo[ 1,5-a]pyrazine, 1 -bromo-3-methyl-hydrolysis, S, 625 reactivity, 5, 625... 

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