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Breaking and Making of Rings: A Method for the Preparation of 4‐Quinolone‐3‐carboxylic Acid Amides and the Expensive Drug Ivacaftor
Author(s) -
Vasudevan N.,
Jachak Gorakhnath R.,
Reddy D. Srinivasa
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501048
Subject(s) - chemistry , combinatorial chemistry , ring (chemistry) , indole test , acetic acid , quinolone , organic chemistry , drug , carboxylic acid , pharmacology , biochemistry , antibiotics , medicine
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.