ChemInform Abstract: SYNTHESIS OF 4‐SUBSTITUTED‐3‐HYDROXY‐2‐QUINOLONES AND AZINES

Abstract

Bei der Reaktion von Isatin (I) mit Diazomethan‐Derivaten (II) werden die 3‐Hydroxy‐2‐chinolone (III) neben den Azinen (IV) gebildet.

Discovery, SAR, and Pharmacokinetics of a Novel 3-Hydroxyquinolin-2(1H)-one Series of Potent d-Amino Acid Oxidase (DAAO) Inhibitors

“…The construction of the quinolinone ring has recently been reviewed, 16 and several syntheses of compound 2 have been reported in the literature: (a) ring expansion reaction of isatin with diazomethane, 17 (b) Eistert ring expansion of isatin with ethyl diazoacetate, 18 and (c) treatment of 2-aminobenzaldehyde with chloroacetic anhydride. 19 In addition, syntheses of some chloro (7, 17 8, 20 and 9 19 ), methyl (13, 19 23, 21 24, 22 and 25 23 ) and pyridyl (18 24 ) analogues of 2 have also been reported (see Table 1 for structures). Modified versions of the literature routes for 2 starting from the appropriate isatin were used for the preparation of compounds 2-5, 7-12, 14-17, and 26-27 (Scheme 1).…”