Tetrahedron

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 ...

Efficient ligand-free copper-catalyzed N-arylation of amides...

[Yong, Fui-Fong; Teo, Yong-Chua; Chua, Guan-Leong; Lim, Gina Shiyun; Lin, Yizhen Tetrahedron Letters, 2011 , vol. 52, # 11 p. 1169 - 1172]

A versatile synthesis of tricyclic analogues of quinolone an...

[Michael, Joseph P.; De Koning, Charles B.; Stanbury, Trevor V. Tetrahedron Letters, 1996 , vol. 37, # 52 p. 9403 - 9406]

Conformational analysis of rotational barriers in N-arylpyrr...

[Billing, D. G.; Boeyens, J. C. A.; Denner, L.; Plooy, K. E. Du; Long, G. C.; Michael, J. P. Acta Crystallographica, Section B: Structural Science, 1991 , vol. 47, # 2 p. 284 - 288]