Breaking and making of rings: a method for the preparation of 4-quinolone-3-carboxylic acid amides and the expensive drug ivacaftor

TitleBreaking and making of rings: a method for the preparation of 4-quinolone-3-carboxylic acid amides and the expensive drug ivacaftor
Publication TypeJournal Article
Year of Publication2015
AuthorsVasudevan, N, Jachak, GR, D. Reddy, S
JournalEuropean Journal of Organic Chemistry
Issue34
Pagination7433-7437
Date PublishedDEC
ISSN1434-193X
KeywordsAmides, Drug design, Fused-ring systems, Oxidation, Ozonolysis
Abstract

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.

DOI10.1002/ejoc.201501048
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)3.068
Divison category: 
Organic Chemistry