Synthesis of 4-Hydroxyquinolines. VI. Synthesis of 3-n-Heptyl-7-methoxy-2-methyl-4-quinolinol¹

Abstract

Synthesis of 4-Hydroxyquinolines. VI. Synthesis of 3-n-Heptyl-7-methoxy-2methyl-4-quinolinol1

Creation of 4-Quinolone Thioether and Selenoether Derivatives via Pd-NHC Catalysed Cross-Coupling Reaction

“…Representative examples of important biologically active scaffolds containing C-S and C-Se linkages 4-Quinolones frequently feature in pharmaceutical chemistry exhibiting properties such as antibacterial, 11 antimalarial, 12 and anticancer activities. 13 As a consequence, the synthesis of 4-quinolones and their derivatives has received considerable interest and various synthetic procedures are available in the literature.…”

Recent Advances in the Synthesis of N-Containing Heteroaromatics via Heterogeneously Transition Metal Catalysed Cross-Coupling Reactions

“…Among the different methods described for the synthesis of 2-substituted-4-quinolones [ 87 , 88 , 89 , 90 , 91 , 92 , 93 , 94 , 95 , 96 , 97 , 98 , 99 , 100 , 101 , 102 , 103 ], the palladium catalyzed carbonylative coupling of 2-iodoanilines with arylacetylenes, initially reported by Torii and co-workers [ 26 , 104 ], appears to be the most versatile. These authors obtained good yields towards the expected compounds using homogeneous [PdCl 2 (PPh 3 ) 2 ] or [PdCl 2 (dppf)] (5 mol %) in presence of an excess of diethylamine which plays a key role in the cyclization step.…”

“…The rich structural diversity encountered in these compounds, in addition to their biological and pharmaceutical relevance, have motivated more than 100 years of research aiming at developing economical, efficient and selective synthetic strategies for these compounds [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 ]. For example, as far as indoles are concerned, these methodologies include the Fisher synthesis from aryl hydrazones [ 9 , 14 ], the Batcho-Limgruber synthesis from o -nitrotoluenes and dimethylformamide acetals [ 15 ], the Gassman synthesis from N- haloanilines [ 16 , 17 ] or the Madelung cyclisation of N -acyl- o -toluidines [ 18 ].…”

“…For example, as far as indoles are concerned, these methodologies include the Fisher synthesis from aryl hydrazones [ 9 , 14 ], the Batcho-Limgruber synthesis from o -nitrotoluenes and dimethylformamide acetals [ 15 ], the Gassman synthesis from N- haloanilines [ 16 , 17 ] or the Madelung cyclisation of N -acyl- o -toluidines [ 18 ]. For quinolones, a less developed area, the most remarkable methodologies include the condensation of anilines with β-ketoesters followed by cyclisation [ 10 , 11 , 12 ] or the heterocyclisation of 2-aminochalcones [ 13 ]. The classical approaches generally reported for indoxyl synthesis include the condensation of o -nitrobenzaldehydes with cyclic ketones under basic conditions [ 19 ], the base induced intramolecular cyclisation of o -azidophenyl sec -alkylketones [ 20 ] or the acid promoted cyclisation of 2-diazo-2'-( p -tolylsulphonylamino)acetophenones [ 21 ].…”

Antimalarial Agents IX

“…The 7-chloro analog of endochin, 7-chloro-3heptyl-2-methyl-4-quinolone (IV), was synthesized according to the general procedure of Leonard, Herbrandson, and Van Heynigen (22). The condensation of m-chloroaniline and ethyl acetoacetate proceeded smoothly to give ethyl 0-m-chloro-anilinocrotonate (XI) in 81% yierd.…”