Oxidation quinoline

Among the aromatics, it was found that 4-nitroquinoline N-oxide [56-57-5] is a powerful carcinogen producing malignant tumors when painted on the skin of mice (80). It was further estabUshed that the 2-methyl, 2-ethyl, and 6-chloro derivatives of 4-nitro quinoline oxide are also carcinogens (81). 

Dinitroquinoline derivative 94 under alkaline conditions condensed to give tri-azolo[4,5-c]quinoline oxide 95. On the other hand, heating 94 in aqueous acetic acid is reported to provide 50% yield of 96 (Scheme 15) (80M963). 

Ferrihydrite catalysis of hydroxyl radical formation from peroxide has also shown experimental results consistent with a surface reaction [57]. The yield of hydroxyl radical formation was lower for ferrihydrite than for dissolved iron, resulting in a higher peroxide demand to degrade a given amount of pollutant. As mentioned above, although ferrihydrite exhibited a faster rate of peroxide decomposition than goethite or hematite, the rate of 2-chlorophenol degradation with these catalysts was fastest for hematite [55], In other studies, quinoline oxidation by peroxide was not observed when ferrihydrite was used as catalyst [53]. 

The Intermediate In this synthesis of disparlure, (Z)-2-tridecenol, Is obtained by hydrogenation of 2-trldecynol In the presence of a palladium catalyst poisoned with barium sulfate and quinoline. Oxidation of (Z)-2-tridecenol with tert-butyl hydroperoxlde/tItanium tetralsopropoxlde/D (-)-diethyl tartrate gives (2R, 3S)-epoxytrldecanol In enantiomeric excess reported to be as much as 98 percent after recrystalllzatlon. 

Treatment of the Reissert compound derived from 4-chloroisoquinoline with phosphorus pentachloride yielded 4-chloro-l-cyanoisoquinoline. Similar treatment of the benzo[/]quinoline Reissert compound gave a mixture of nitrile and amide." The Reissert compound from 2-bromo-benzo[/]quinoline with thionyl chloride gives 2-bromo-3-cyanobenzo-[/]quinoline." Oxidation of a Reissert compound in the presence of 50% sodium hydroxide and a phase transfer catalyst also gives the isoquinaldonitrile. ... 

DNA sequence of 12 million nucleotides and 6000 genes has been determined.165 It can be used to reduce /3-ke-toesters in petrol plus a small amount of water to the S alcohol ester in 100% conversion with more than 98%ee.166 When only water is used as the medium, the enantioselec-tivity is reduced greatly.167 In contrast with baker s yeast and Geotrichum candidum,168 which produce the S alcohols from the reduction of ketones, Yarrowia lipolytica gives the R isomer, but in only moderate yields.169 Pichia farinosa also produces the R isomer.170 (For more on the preparation of single optical isomers, see Chap. 10.) Other reductions can also be carried out with baker s yeast as shown in 9.15 for the quinoline oxide.171... 

These compounds are convenient starting materials for the preparation of a wide variety of platinum(II) complexes. The chlorine atoms can be replaced by other negative groups such as bromide, iodide, hydroxide, nitrate, nitrite, and thiocyanate. The ammonia molecules can be replaced by other bases such as pyridine, arylamines, and quinoline. Oxidation with aqua regia or chlorine yields the corresponding isomers of tetrachlorodiammineplatinum(IV) (synthesis 62). A supposedly third (7-) form has been shown to be a solid solution or mixture of the cis (jS-) and trans (a-) isomers. 

It should be pointed out that this reaction is of general nature and it can be used for the synthesis of different types heteroarenes, including derivatives 94-95 obtained in the reaction of quinoline oxide with chlorotrifluoroethylene and 2-7/-pentafluoro-propene, respectively (Fig. 7.31). ... 

Kobayashi et al. reported the synthesis of 2-, 3- and 4- trifluoromethyl- quinoline oxides, having quite different chemical properties. While in the reaction 2-CF3-quinoline with P(0)Cl3 gave 4-chloro-2-CF3-quinoline, 3- and 4-CF3 isomers selectively produce the corresponding 2-chloro- derivatives. ... 

The classic SnAt substitution of activated aryl halides by protected cyanohydrin anions provides substituted benzophenones. Another procedure for the arylation of protected cyanohydrin anions involves the use of aromatic substrates activated as their Tr-chromium tricarbonyl complexes. Addition of the anion of (32) to the 1,3-dimethoxybenzene complex, for example, leads principally to the meta-sub-stituted isomer (33 equation 20). I eferential meta regioselectivity is also noted with other ir-chromium tricarbonyl complexes of arenes. Other arylations of cyanohydrin anions include interesting but synthetically limited additions at the a-position of quinoline -oxides. In a similar manner, cyanohydrin carbonates of aromatic aldehydes react with A -oxides of quinoline and isoquinoline. ... 

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