186667-91-4Relevant academic research and scientific papers
Reformatsky reactions with N-arylpyrrolidine-2-thiones: Synthesis of tricyclic analogues of quinolone antibacterial agents
Michael, Joseph P,De Koning, Charles B,Hosken, Gladys D,Stanbury, Trevor V
, p. 9635 - 9648 (2007/10/03)
A convenient synthesis of 5-oxo-1,2,3,5-tetrahydropyrrolo[1,2-α]quinoline-4-carboxylic acids, tricylic 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-thione 18, and cyclisation of the resulting diethyl pyrrolidinylidenemalonate intermediates 19 in polyphosphoric acid. The products proved to be devoid of biological activity.
A versatile synthesis of tricyclic analogues of quinolone antibacterial agents: Use of a novel Reformatsky reaction
Michael, Joseph P.,De Koning, Charles B.,Stanbury, Trevor V.
, p. 9403 - 9406 (2007/10/03)
A simple synthesis of tricyclic analogues of the quinolone antibiotics bearing a diverse range of substituents on the aromatic ring is described. The key steps involve unprecedented Reformatsky reaction between diethyl bromomalonate and N-arylpyrrolidine-2-thiones 8, followed by cyclisation of the resulting enaminone intermediates 9 in polyphosphoric acid.
