Reformatsky reactions with N-arylpyrrolidine-2-thiones: synthesis of tricyclic analogues of quinolone antibacterial agents

A convenient synthesis of 5-oxo-1,2,3,5-tetrahydropyrrolo[1,2- a]quinoline-4-carboxylic acids, tricyclic analogues of the quinolone antibiotics, is described. Key steps in the route are a novel zinc-mediated Reformatsky reaction between diethyl bromomalonate and N-arylpyrrolidine-2-thiones 18, and c...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2001-11, Vol.57 (47), p.9635-9648
Main Authors: Michael, Joseph P, de Koning, Charles B, Hosken, Gladys D, Stanbury, Trevor V
Format: Article
Language:English
Subjects:
enaminones
quinolones
Reformatsky reaction
thiolactams
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A convenient synthesis of 5-oxo-1,2,3,5-tetrahydropyrrolo[1,2- a]quinoline-4-carboxylic acids, tricyclic analogues of the quinolone antibiotics, is described. Key steps in the route are a novel zinc-mediated Reformatsky reaction between diethyl bromomalonate and N-arylpyrrolidine-2-thiones 18, and cyclisation of the resulting diethyl pyrrolidinylidenemalonate intermediates 19 in polyphosphoric acid. The products proved to be devoid of biological activity. Two key steps in the synthesis, including an atypical Reformatsky reaction with thiolactams, are shown.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(01)00964-4