Reformatsky reactions with N-arylpyrrolidine-2-thiones: synthesis of tricyclic analogues of quinolone antibacterial agents
JP Michael, CB de Koning, GD Hosken, TV Stanbury
Index: Michael, Joseph P; De Koning, Charles B; Hosken, Gladys D; Stanbury, Trevor V Tetrahedron, 2001 , vol. 57, # 47 p. 9635 - 9648
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Citation Number: 85
Abstract
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 ...
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