ORGN 237 |
| Organosulfur compounds are useful intermediates in organic synthesis. Extrusion reactions are characteristic of organic sulfides, sulfoxides and sulfones although only limited utility was found in synthesis of complex molecules. In our continuing effort to design and synthesize novel heterocyclic scaffolds, we investigated the sequential oxidations of side chain sulfur and the ring one in 4-arylthiopyrimido[4,5-b][1,4]benzothiazepines. By controlling the reaction temperature and the amount of oxidants, sequential oxidations of the side chain sulfur and ring one in the forms of sulfoxide and sulfone could be achieved in moderate yields, respectively. Subsequently, the extrusion reaction of sulfur monoxide in 4-aminopyrimido[4,5-b][1,4]benzothiazepines occurred under heating in toluene to give pyrimido[5,4-c]isoquinolines. The strategy of sequential sulfur oxidation and extrusion of 4-arylthiopyrimido[4,5-b][1,4]benzothiazepines has been successfully applied to the preparation of a class of biologically and pharmaceutically interesting 4-aminopyrimido[5,4-c]isoquinolines.
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster
Sci-Mix
Division of Organic Chemistry |
