Acetylenchemie 7. Mitt.: Mechanistische Studien zur Synthese von Pyrano-[3,2-c]chinolin-Alkaloiden aus 4-Hydroxychinolin-2-onen und 3-Chlor-3-methylbut-1-in

Synthesis and Chemical Reactivity of Pyrano[3,2‐c]quinolinones

“…Phase‐transfer catalyzed reaction of 4‐hydroxyquinolin‐2(1 H )‐one 2 with 3‐chloro‐3‐methylbut‐1‐yne ( 53 ) gave pyrano[3,2‐ c ]quinoline 42 , beside furo[3,2‐ c ] quinolinone 54 as by‐product (Scheme ).…”

Sulfone-Mediated SNAr Reaction as a Powerful Tool for the Synthesis of 4-Quinolinyl Ethers and More—Application to the Synthesis of HCV NS3/4a Protease Inhibitor BI 201420

“…Transition-metal-catalyzed aryl ether formation has been a rapidly developing area in recent years, , but application to 4-quinoline ethers has been very rare, probably partly because quinoline-promoted ligand exchange can destroy some catalyst complexes. So far, the most frequently employed method in drug discovery is via alkylation of 4-hydroxyquinolines (S N 2 approach, Scheme ), but it has the following limitation and drawbacks. (1) The regio-selectivity of O-alkylation versus N-alkylation is poor and difficult to control, , unless one position is totally blocked.…”