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Note | Regular issue | Vol 57, No. 9, 2002, pp.1659-1682
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9522
Syntheses of 3-Aminoquinoline-2,4(1H,3H)-diones

Stanislav Kafka, Antonín Klásek,* Jirí Polis, and Janez Kosmrlj

*Faculty of Technology, Tomas Bata University in Zlín, 762 72 Zlín, Czech Republic

Abstract

Reaction of 3-chloro- (2) and 3-bromoquinoline-2,4(1H,3H)-diones (3) with excess of primary alkyl- or arylamines in dimethylformamide provides the corresponding 3-alkyl- or 3-arylamino derivatives (4). Compounds (4) with the primary amino group at the 3 position were best prepared by reaction of 2 with in situ generated ammonia under anhydrous conditions. An alternative approach to the primary amines (4) via reduction of 3-azidoquinoline-2,4(1H,3H)-diones (5) was investigated. The reduction of 5 with zinc in acetic acid gave moderate to good yields of the desired products, while the reaction with triphenylphosphine afforded exclusively 4-hydroxyquinolin-2(1H)-one (1).