One-Pot Oxidative Synthesis of Substituted Quinolines from Alcohols and Arylamines Catalyzed by Fe(CrO2)2 in Water Medium
One-pot tandem synthesis was developed for substituted quinolines (in up to 97% yields) involving a selective catalytic oxidation of primary amines to aldehydes and their condensation with arylamines under the action of a dispersion of Fe(CrO2)2 and water solution of H2O2 at room temperature. The stage of catalytic oxidation of alcohols was accelerated by photoactivation. A presumable mechanism of the photoactivated tandem synthesis of 2-methylquinoline was suggested. Catalyst Fe(CrO2)2 was prepared by photochemical synthesis.
Makhmutov
p. 1166 - 1172
(2018/10/24)
Fe(CrO2)2-catalyzed, photoactivated oxidative one-pot tandem synthesis of substituted quinolines from primary alcohols and arylamines
[Figure not available: see fulltext.] A one-pot tandem synthesis of substituted quinolines involving selective catalytic oxidation of primary alcohols to the corresponding aldehydes and their subsequent condensation with arylamines has been developed. Fe(CrO2)2 has been used as a catalyst, and oxidation has been performed with aqueous H2O2. To accelerate the catalytic oxidation of alcohols, photoactivation method has been applied.
Makhmutov, Aynur R.,Mustafin, Akhat G.,Usmanov, Salavat M.
p. 369 - 374
(2018/05/28)
LnCl3·6H2O crystal hydrates as highly effective catalysts in the synthesis of alkyl-substituted quinolines and phenanthrolines
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Bulgakov,Kuleshov,Makhmutov,Dzhemilev
p. 1573 - 1575
(2007/10/03)
SYNTHESIS OF SUBSTITUTED QUINOLINES VIA THE CONDENSATION OF ANILINES WITH ALIPHATIC AND AROMATIC ALDEHYDES IN THE PRESENCE OF TRANSITION METAL AND RARE-EARTH METAL CATALYSTS
Novel catalyst complexes derived from transition metal and rare-earth metal compounds have been developed for the condensation of anilines with aliphatic and aromatic aldehydes to give the corresponding 2,3-disubstituted quinolines in high yields.
Dzhemilev, U. M.,Selimov, F. A.,Khusnutdinov, R. A.,Fatykhov, A. A.,Khalilov, L. M.,Tolstikov, G. A.
p. 1248 - 1253
(2007/10/02)
Base-initiated oxidation of alkylindeneanilines by oxygen
Oxidation and alkylation processes compete in the oxidative transformation of alkylindeneanilines in an alkaline medium.Oxidation leads mainly to the formation of formanilide anbd the corresponding carbonyl compound.Alkylation leads to a product which easily eliminates the aniline molecule with the formation of a derivative of the 1-aza-1,3-diene.A combination of alkylation and oxidation led to derivatives of quinoline.It is assumed that the alkylation-dehydrocyclization-elimination of alkylindeneanilines to quinolines by the action of oxygen and alkali is a variant of the Doebner-Miller reaction.During oxidation in the presence of sodium borohydride the products from conjugate oxidation-reductiono, i.e., the α-imino and β-amino alcohols, are also formed in addition to quinolines and oxidation and alkylation products.
Grigoryan, G. S.,Tovmasyan, V. S.,Malkhasyan, A. Ts.,Martirosyan, G. T.,Beletskaya, I. P.
p. 50 - 56
(2007/10/02)
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