4- quinoline l-oxide

The work of Okamoto et on quinoline and quinoline-l-oxides (Table XI) provides the following relation of solvent to the rate of reaction with piperidine A 7oo/ aic. = 1.5-2.5 x = 80-200 x A benzene-... 

The identification of C8-guanyl and N6-adenyl adducts of 4-aminoquinoline-l-oxide (102,103) in DNA modified by the metaboli-cally-generated 0-seryl ester and the similarity of the adduct profile with that obtained on reaction of DNA with N-acetoxy-4-araino-quinoline-l-oxide suggest an electrophilic reaction mechanism similar to that for the N-acetoxy or N-sulfonyloxy arylamines (Figures 4 and 5). However, N-seryloxy or N-prolyloxy arylamines have not been synthesized and the decomposition products of the esters generated in vitro have not yet been studied. 

Analogous to its reaction with carbonyl compounds (see 6.3.4), benzyltrimethyl-silane undergoes a fluoride-induced nucleophilic substitution reaction on pyridine-1-oxides and quinoline-l-oxide to form 2-benzylpyridines (>70%) and 2-benzyl-quinoline (65%), respectively [57], Allyltrimethylsilane reacts with pyridine-l-oxide to produce 2-propenylpyridine (56%). 

Cyano-3-trifluoromelhyl- E7a. 444f. (3-CF3-quinolin-l-oxide + Ar—CO —Cl/HCN) 4-Dicthylamino-3-mcthyl-2-trifluoro-mcthyl- E7a, 380f. (2-CF3 —4-oxo —4H-3,1-benzoxazine +... 

Quinoline-l-oxide undergoes nitration at the 2-, 5-, and 8-positions. While it is known that isomer ratios are temperature dependent, it has been recently shown that the orientation of nitration is also dependent on the acidity of the reaction medium <1997CPB279>. 2-Nitroquinoline 1-oxide, arising from nitration of unprotonated substrate, predominates under weakly acidic conditions. Nitration in stronger acidic media occurs on the hydroxyquinolinium ion and yields 5- and 8-nitroquinoline 1-oxide as the major products with increasing amounts of the 5-isomer formed in very highly acidic media. 

Benzoxazepin 2-Cyan- E9d, 307 (1-CN — isoquinolin-2-oxid/hv) 3,1-Benzoxazepin 2-Cyan- E9d, 308 (2-CN-quinolin-l-oxid/hv)... 

Dinitro-l-hydroxy- X/l. 834 Quinolin-l-oxid 6-Carboxy-4-nitro-... 

Chlor-4-hydroxy-8-methoxy- E7a, 408 (3-COOH > 3-H) 7-Chlor-4-hydroxy-6-methoxy- E7a, 408 (2-COOH - 2-H) Quinolin-l-oxid 7-Chlor-4-hydroxy-2-methyl- E7a, 512 (N-Oxidat.)... 

N-Ethoxy- E16a, 219 (O-Alkylier.) 2-(2-Hydroxy-ethyl)- XI/2, 314 Propinsaure 2-Amino-5-methoxy-E9a, 695 (N02 - NH2) Quinolin-l-oxid 2,4-Dihydroxy-3-methyl- E7a, 504 [2-NOz—Ar— CO-CH(CH3)-CHO + Boranat Pd —C]... 

Pyrimidin 6-Amino-2,4-dioxo-3-phenyl-l,2,3,4-tetrahydro- E15/2, 2228 [ —R—OH(Cyclokond.)] lH- 6-Nitro-2,3-dihydro- IV/la, 182 Quinolin 4-Hydrazino-6,7-methylen-dioxy- E16a, 700 (Cl - NH-NH2) Quinolin-l-oxid 2-Amino-3-aminocarbonyl- E7a, 504 [2-N02 - Ar -CH = C(CN) -CO —NH2/Pt]... 

Quinolin-l-oxid 2-Cyan-4-methyl-E7a, 512 (N-Oxidat.) Quinolo[8,7-c -l,2-oxazol 3-Methyl-E8a, 396 (8-N02-7-(C0-CH3) —quinolin/SnCl2]... 

Quinolin-l-oxid 2-Cyan-5-methoxy-carbonyl- E7a, 512 (N-Oxidat.)... 

Quinolin-l-oxid 2-Amino-3-cyan-4-ethoxycarbonyl- E7a, 509 [l-Acyloxy-2-oxo-3-(dicyan-methylen)-2,3-H2-indol 4-R-OH]... 

Quinolin-l-oxid 6-Brom-3-ethoxy-carbonyl-4-hydroxy-2-methyl-E7a, 507 (2-N02-Ar-CH0 + H3C-CO-CH2-COOR)... 

Quinolin-l-oxid 4-Isopropyloxy-6-methyl- E7a, 525 (Cl OR) Zimtsiiure -morpholid E5, 937 (En-CHO + Amin/Pd)... 

Benzo [h] quinoline is metlylated at 70°C by the methylsulphinyl carbanion at the 4-, 5- and 6-positions. The same reagent converts benzo[h]quinoline-l-oxide into phenanthrene (Y. Hamada and K. Takeuchi, J. org. Chem., 1977, 4209). 

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