O. N. Chupakhin, Yu. A. Azev, S. G. Alexeev, S. V. Shorshnev, E. Tsoi, V. N. Charushin, “Reactions of <i>N</i>-Aminoquinolones with Ketones: A New Approach to the Synthesis of Tricyclic 6-Fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acids”, Mendeleev Commun., 1992, Volume 2, Issue 4,Pages <nobr>151

This article is cited in 10 papers

Reactions of N-Aminoquinolones with Ketones: A New Approach to the Synthesis of Tricyclic 6-Fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acids

O. N. Chupakhin^a, Yu. A. Azev^b, S. G. Alexeev^c, S. V. Shorshnev^b, E. Tsoi^d, V. N. Charushin^d

^a I. Ya. Postovsky Institute of Organic Synthesis, Urals Branch of the Russian Academy of Sciences, Ekaterinburg, Russian Federation
^b Ural Scientific Research Institute of Technology of Medical Preparations, Ekaterinburg, Russian Federation
^c Urals State Technical University, Ekaterinburg, Russian Federation
^d Department of Organic Chemistry, Urals State Technical University, Ekaterinburg, Russian Federation

Abstract: Reactions of 7-(X)-substituted ethyl 1-amino-4-oxo-1,4-dihydroquinoline-3-carboxylates (1a-c; X = F, Cl and 4-methylpiperazin-1-yl) with mono- and di-ketones have been studied. Treatment of 1a; X = F with cyclopentanone and cyclopentanone in acetic acid resulted in the corresponding azomethynes; α-dicarbonyl compounds such as glyoxal, glyoxylic acid or ethyl pyruvate caused desamination of 1a into ethyl, 6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate, while reactions of 1a-c with acetoacetone resulted in tricyclic 7-fluoro-4-oxopyrazolo[1,5-a]quinoline-4-carboxylic acids

Language: English

DOI: 10.1070/MC1992v002n04ABEH000180