81355-39-7Relevant academic research and scientific papers
An efficient catalytic method for the Friedl?nder annulation mediated by peptide coupling agent propylphosphonic anhydride (T3P)
Augustine, John Kallikat,Bombrun, Agnes,Venkatachaliah, Srinivasa
experimental part, p. 6814 - 6818 (2012/01/03)
We have demonstrated the utilization of T3P, a mild and low toxic peptide coupling agent, as a promoter and water scavenger in the Friedl?nder annulation, and thus introduced a highly efficient catalytic process to access carbocyclic and heterocyclic fused quinolines under microwave irradiation or a conventional heating technique. The reaction conditions are sufficiently mild to tolerate the acid and base sensitive functional groups that can serve as levers for further extension of the quinoline products.
The Reactions of Some ortho-Substituted Anilines With Various α,β-Acetylenic Ketones. A Route to Substituted Quinolines
Sinsky, M. S.,Bass, R. G.
, p. 759 - 768 (2007/10/02)
The reactions of some ortho-substituted anilines with various α,β-acetylenic ketones were investigated as a route to 4-alkyl-, 4-aryl-, 4-hydroxy-, and 4-amino-3-quinolyl ketones.The anilines examined were 2-aminoacetophenone (1), 2-aminobenzophenone (2), anthranilonitrile (3), methyl anthranilate (4), and ethyl anthranilate (5).The acetylenic ketones used were 1,4-diphenyl-2-butyne-1,4-dione (6), 3-butyn-2-one (7), 1,3-diphenyl-2-propyn-1-one (8), and 4-phenyl-3-butyn-2-one (9).The acetylenic ketones typically reacted with the anilines to give enamines; however, exceptions were found.Acetylene 6 reacts with 3 to give the enamine (13) along with a small amount of 2,3-dibenzoyl-4-quinolamine (14).The reactions of 1 or 2 with 6 give the respective quinoline derivatives directly.Acetylene 8 reacts with 2 to give 3-benzoyl-2,4-diphenylquinoline (22) directly, whereas no reaction occurs between 8 and 1 or 3.Acetylene 9 does not react with 1, 2 or 3.The enamines exist as the intramolecularly hydrogen bonded isomers and usually undergo cyclization with 5 molar equivalents of methanolic sodium methoxide to give quinoline derivatives.The 4-quinolinols exist predominantly as the 4-quinolinone tautomer.
SELECTIVE REDUCTION. REACTION OF 3,4-DICARBOMETHOXYQUINOLINE WITH LITHIUM ALUMINIUM HYDRIDE.
Godard, A.,Queguiner, G.
, p. 4813 - 4814 (2007/10/02)
The selective reduction of 3,4-dicarbomethoxyquinoline by lithium aluminium hydride at low temperature affords only the unexpected 3-formyl 4-carbomethoxy quinoline.The difficulty of reduction of the usually more reactive 4-ester group can be explained by a steric hindrance by the H5 peri proton on one side and by the 3-ester group on the other side.
