Transformations of imidazo[4, 5-f]quinoline
Treatment of imidazo[4, 5-f]quinoline and some of its 3-substitmion products with methyl halides and methyl benzenesulfonate gives as the main reaction products N-methylimidazoquinolinium salts, which can also be synthesized from 5, 6-dimainoquinolines. Methylation at the N atom of the imidazole ring is only a side reaction. Treatment with trimethylphenylammonium hydroxide introduces a methyl radical into the NH group of imidazoquinoline, giving a mixture of 1-and 3-substitution products.
KeywordsMethyl Hydroxide Organic Chemistry Imidazole Halide
Unable to display preview. Download preview PDF.
- 1.R. Huisgen, Ann., 559, 101, 1948.Google Scholar
- 2.B. I. Khristich and A. M. Simonov, KhGS, 611, 1966.Google Scholar
- 3.V. M. Rodionov, Bull. soc. chim. [Chemistry of Heterocyclic Compounds], France, 45, 109, 1929.Google Scholar
- 4.A. M. Simonov, ZhOKh, 22, 2006, 1952.Google Scholar
- 5.W. La Coste, Ber., 15, 1918, 1882.Google Scholar
- 6.A. Kaufmann and O. Zeller, Ber., 50, 1629, 1917.Google Scholar
- 7.W. C. J. Ross, J. Chem. Soc., 223, 1948.Google Scholar
- 8.A. Claus and L. Schnell, J. pr. Chem., 53, 119, 1896.Google Scholar
- 9.W. O. Sykes, J. Chem. Soc., 4430, 1965.Google Scholar