4286-69-5Relevant academic research and scientific papers
Facile three-component synthesis of substituted quinolines catalyzed by iridium(III) complex
Nakajima, Takayuki,Inada, Takashi,Igarashi, Takeyuki,Sekioka, Tadashi,Shimizu, Isao
, p. 1941 - 1949 (2007/10/03)
A convenient and efficient synthesis of substituted quinolines via a simple one-pot reaction of an aniline, an aromatic aldehyde, and an enolizable aliphatic aldehyde in the presence of the iridium catalyst [IrCl 2H(cod)]2 under oxygen as an oxidant was developed. The reaction proceeds with Mannich-type imine formation followed by nucleophilic addition to give β-amino aldehydes. Dehydrative cyclization takes place to give dihydroquinoline, which is then dehydrogenated by aerobic oxidation to give 2-aryl-3-alkylquinolines. Dialkylquinolines were obtained by the reaction with anilines and aliphatic aldehydes in good yields.
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
Dzhemilev, U. M.,Selimov, F. A.,Khusnutdinov, R. A.,Fatykhov, A. A.,Khalilov, L. M.,Tolstikov, G. A.
, p. 1248 - 1253 (2007/10/02)
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.
Base-initiated oxidation of alkylindeneanilines by oxygen
Grigoryan, G. S.,Tovmasyan, V. S.,Malkhasyan, A. Ts.,Martirosyan, G. T.,Beletskaya, I. P.
, p. 50 - 56 (2007/10/02)
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.
