17282-82-5Relevant academic research and scientific papers
Sulfamic acid supported on Fe3O4@SiO2superpara magnetic nanoparticles as a recyclable heterogeneous catalyst for the synthesis of quinolines
Nasseri,Zakerinasab,Samieadel
, p. 41753 - 41762 (2014)
In the present study, for the first time the synthesis of sulfamic acid supported on Fe3O4@SiO2superpara magnetic nanoparticles as a solid acid catalyst with large density of sulfamic acid groups was suggested. The structu
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.
