4-HYDROXY-2-QUINOLONES. 204. SYNTHESIS, BROMINATION, AND ANALGETIC PROPERTIES OF 1-ALLYL-4-HYDROXY-6,7-DIMETHOXY-2-OXO-1,2-DIHYDROQUINOLINE-3-CARBOXYLIC ACID ARYLALKYLAMIDES

Authors

  • И. В. Украинец National University of Pharmacy
  • Е. В. Моспанова Institute of Chemical Technology, Vladimir Dal' Eastern Ukraine National University
  • Н. А. Джарадат Pharmaceutical College, An-Najah National University
  • О. В. Бевз National University of Pharmacy
  • А. В. Туров Taras Shevchenko Kyiv National University

DOI:

https://doi.org/10.1007/942

Keywords:

4-hydroxy-2-oxo-1, 2-dihydroquinoline-3-carboxamides, amidation, analgesic activity, bromination, halocyclization

Abstract

A simple method has been proposed and used for the preparation of 1-allyl-4-hydroxy-6,7-dimethoxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid arylalkylamides. Similar to alkylamides of this acid, the arylalkylamides obtained are halogenated with cyclization by one equivalent of molecular bromine to give the corresponding 2-bromomethyl-7,8-dimethoxy-5-oxo-1,2-dihydro-5H-oxazolo[3,2-a]quinoline-4-carboxamides. However, the reaction proceeds quite differently when using an excess of bromine. After the usual initial oxazole ring closure, the excess bromine brominates the aromatic ring of the amide fragment. The results of testing for the analgesic activity of these products are presented.

Authors: I. V. Ukrainets, E. V. Mospanova, N. A. Jaradat, O. V. Bevz, and A. V. Turov

English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (9), pp 1347-1356

http://link.springer.com/article/10.1007/s10593-012-1143-7

 

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Published

2013-09-06

Issue

No. 9 (2012)

Section

Original Papers