%0 Journal Article %J European Journal of Organic Chemistry %D 2015 %T Breaking and making of rings: a method for the preparation of 4-quinolone-3-carboxylic acid amides and the expensive drug ivacaftor %A Vasudevan, N. %A Jachak, Gorakhnath R. %A Reddy, D. Srinivasa %K Amides %K Drug design %K Fused-ring systems %K Oxidation %K Ozonolysis %X

A simple and convenient method to access 4-quinolone-3-carboxylic acid amides from indole-3-acetic acid amides through one-pot oxidative cleavage of the indole ring followed by condensation (Witkop-Winterfeldt type oxidation) was explored. The scope of the method was confirmed with more than 20 examples and was successfully applied to the synthesis of the drug Ivacaftor, the most expensive drug on the market.

%B European Journal of Organic Chemistry %I WILEY-V C H VERLAG GMBH %C POSTFACH 101161, 69451 WEINHEIM, GERMANY %P 7433-7437 %8 DEC %G eng %N 34 %3

Foreign

%4 3.068 %R 10.1002/ejoc.201501048