Abstract
The hydroxylation of 1-alkyl-3-(2-quinolyl)quinolinium halides by an alkaline solution of K3[Fe(CN)6] in aqueous 1,4-dioxane leads to a mixture of 1-alkyl-3-(2-quinolyl)-1,2-dihydro-2-quinolones and 1-alkyl-3-(2-quinolyl)-1,4-dihydro-4-quinolones with predominance of the former. The use of the system of K3[Fe(CN)6]/Mg(OH)2 in aqueous 1,4-dioxane leads to the regiospecific formation of 1-alkyl-3-(2-quinolyl)-1,4-dihydro-4-quinolones.
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REFERENCES
A. V. Aksenov and O. N. Nadein, Khim. Geterotsikl. Soedin., 1527 (2000).
A. V. Aksenov, I. V. Magedov, and Yu. I. Smushkevich, J. Chem. Soc., Perkin Trans., 1, 759 (1992).
A. V. Aksenov, O. N. Nadein, I. V. Borovlev, and Yu. I. Smushkevich, Khim. Geterotsikl. Soedin., 1218 (1998).
F. Kröhnke and H. Dickhäuser, and I. Vogt, Liebigs Ann. Chem., 644, 93 (1961).
J. W. Bunting and W. G. Meathrel, Canad. J. Chem., 52, 303 (1974).
I. S. Poddubnyi, Khim. Geterotsikl. Soedin., 774 (1995).
A. V. Aksenov, I. V. Aksenova, I. V. Borovlev, A. A. Bumber, A. F. Pozharskii, and Yu. I. Smushkevich, Khim. Geterotsikl. Soedin., 1391 (1996).
I. V. Romanenko, N. A. Klyuev, and A. K. Sheinkman, Voprosy Khimii i Khimicheskoi Tekhnologii, No. 57, 78 (1979).
J. Sharp, I. Gosin, and A. Rolley, Organic Chemistry Laboratory Textbook[Russian translation], Mir, Moscow (1993), p. 193.
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Nadein, O.N., Aksenov, A.V. Investigation of 2,3'-Biquinolyl. 11. Regioselectivity in the Hydroxylation of 1-Alkyl-3-(2-quinolyl)quinolinium Halides. Chemistry of Heterocyclic Compounds 37, 867–871 (2001). https://doi.org/10.1023/A:1012403725287
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DOI: https://doi.org/10.1023/A:1012403725287