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Paper | Regular issue | Vol 45, No. 6, 1997, pp.1097-1110
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7770
Synthesis of N-(1-Aziridinyl)-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acids

Sándor Bátori,* Géza Tímári, András Messmer, Benjámin Podányi, Lelle Vasvári-Debreczy, and István Hermecz

*CHINOIN Pharmaceutical and Chemical Works Ltd., P. O. Box 110, H-1325 Budapest, Hungary

Abstract

A series of N-(1-aziridinyl)quinoline-3-carboxylic acid derivatives (e.g. 11a-f, 20a-g, 21a-d) have been synthesized by insertion reaction of nitrenes (e.g. ethyl 7-chloro-6-fluoro-1-nitreno-1,4-dihydro-4-oxoquinoline-3-carboxylate (9)) into double bond of different olefins (e.g. styrene (10a), see Schemes 2 and 4). The nitrenes were formed in situ by oxidation of N-aminoquinolin-4(1H)-one derivatives (8, 18a,b) using Pb(OAc)4 as oxidizing agent.