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. 2009 Feb 18;50(7):785-789.
doi: 10.1016/j.tetlet.2008.11.121.

Efficient Synthesis of the 2-amino-6-chloro-4-cyclopropyl-7-fluoro-5-methoxy-pyrido[1,2-c]pyrimidine-1,3-dione core ring system

Jonathan D Rosen  1 , Nadezhda German, Robert J Kerns
Affiliations

Efficient Synthesis of the 2-amino-6-chloro-4-cyclopropyl-7-fluoro-5-methoxy-pyrido[1,2-c]pyrimidine-1,3-dione core ring system

Jonathan D Rosen et al. Tetrahedron Lett. .

Abstract

An optimized total synthesis of the 2-amino-6-chloro-4-cyclopropyl-7-fluoro-5-methoxy-pyrido[1,2-c]pyrimidine-1,3-dione core structure of a new fluoroquinolone-like class of antibacterial agents is described. This synthesis is highlighted by a nearly quantitative ring-closing reaction to form the pyrido[1,2-c]pyrimidine core. This bicyclic ring system serves as a scaffold for a family of biologically active compounds.

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Figures

Figure 1
Figure 1
Quinolone-class antibacterial agents. (A) Representative structures of naphthyridone, fluoroquinolone and 2-pyridone type cores. (B) Representative structures of newer quinazoline-dione type cores (R4 = H or NH2)
Scheme 1
Scheme 1
Scheme 2
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Scheme 5
Scheme 5
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