ChemInform Abstract: 4‐Hydroxy‐2‐quinolones. Part 204. Synthesis, Bromination, and Analgetic Properties of 1‐Allyl‐4‐hydroxy‐6,7‐dimethoxy‐2‐oxo‐1,2‐dihydroquinoline‐3‐carboxylic Acid Arylalkylamides.

Abstract

4-Hydroxy-2-quinolones. Part 204. Synthesis, Bromination, and Analgetic Properties of 1-Allyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline--3-carboxylic Acid Arylalkylamides. -A simple method for the synthesis of the title amides (III) (21 examples) is given. Amides (III) undergo facile halocyclization upon addition of one equivalent of molecular bromine [→ (IV)]. Use of excess amounts of bromine results in a tandem halocyclization/electrophilic aromatic substitution [→ (V)]. All new compounds (III) possess analgesic activities. Compound (IIId) and (IIIg) display specific activity superior to that of the commonly used non-narcotic analgesics diclofenac and ketorolac. -(UKRAINETS*, I. V.; MOSPANOVA, E. V.; JARADAT, N. A.; BEVZ, O. V.; TUROV, A. V.; Chem. Heterocycl. Compd. (N. Y., NY, U. S.) 48 (2012) 9, 1347-1356, http://dx.