Methyl quinoline sulfate

The nitration of l,2,5-selenadiazolo[3,4-/] quinoline 77 with benzoyl nitrate affords the 8-nitro derivative 78, whereas methylation with methyl iodide or methyl sulfate afforded the corresponding 6-pyridinium methiodide 79 or methosulfate 80, respectively (Scheme 29). The pyridinium salt 80 was submitted to oxidation with potassium hexacyanoferrate and provided 7-oxo-6,7-dihydro derivative 81 or, by reaction of pyridinium salt 79 with phenylmagnesium bromide, the 7-phenyl-6,7-dihydro derivative 82. Nucleophilic substitution of the methiodide 79 with potassium cyanide resulted in the formation of 9-cyano-6,9-dihydroderivative 83, which can be oxidized by iodine to 9-cyano-l,2,5-selenadiazolo [3,4-/]quinoline methiodide 84. All the reactions proceeded in moderate yields (81IJC648). 

Synthetic a-carbolines have also attracted interest as antitumor agents. For example, Chen and coworkers [97] prepared a series of indolo[2,3-fr] quinoline derivatives, the most active of which was 154, which had a mean GI50 value against three cancer cell lines of 0.78 iM. This compound was prepared by methylation of 153 with dimethyl sulfate (Fig. 43), and was isolated in 12% yield, along with isomeric 155, which was isolated in 40% yield, but had significantly lower cytotoxicity. Precursor 153 itself was found to be inactive. 

Thallin= Tetrahydroparachinanisol—C i.HuNO—isaderi vat i ve of the paramethyl ether of quinolin. It is met with in the form of sulfate and tartrate in the shape of crystalline powders. The odor of the sulfate is similar to that of anisol (methyl phenate) ... 

MW promoted methylation of 6//-indolo[2,3-Z ]quinoline (387) with dimethyl sulfate in DMF at 140 °C to provide 388 in 75% yield within 5 min (Scheme 78) (99S326). 

Draw the major product of a reaction between 3-methyl-l-phenyl-1-hexyne and hydrogen gas in the presence of palladium-on-bar-ium sulfate and quinoline. 

Cl4H20N2O2 f 7-Acetyl-3,5,5,9,9-pentamethyl-1,6-diazabicyclo-[4.3.0]nona-3,7-dien-2-one, 43B, 338 C14H2 2N2O7S, 3-Carbethoxy-1,6-dimethyl-4-OXO-6,7,8,9-tetrahydro-homopyrimidazolium methyl sulfate, 4IB, 330 Cl4H23NO, cis 1,2,3,4,4a,5,6,8a-Octahydro-3,3-dimethyl-1-(1-propyl)-quinolin-2-one, 43B, 338... 

The methylation of pyridine, quinoline, and isoquinoline N-oxides to afford A-methoxy salts has also been investigated. For example, treatment of quinoline A-oxide with dimethyl sulfate provides the N-methoxy methylsulfate salt in excellent yield (eq 9). The resulting salts were subsequently treated... 

Tertiary alkyl and aromatic amines are also conveniently quater-nized using dimethyl sulfate. For example, a series of thioquinan-threnediinium salts for use as potential antibiotics were prepared via methylation of their quinoline precursors using dimethyl sulfate (eq 14). ... 

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