ORGN 599 |
| The synthesis and reactivity of imidazo[5,1-b]thiazol-3-ones (2) and imidazo[5,1-b]thiazin-4-ones (3) for solution phase combinatorial library generation is described. The target compounds can be synthesized in two steps, utilizing a three-component reaction to form a substituted sulfanyl-imidazole ring (1) and a solid supported coupling agent to generate the bi-cyclic products. The reactivity of the fused ring systems to enolization and nucleophilic ring opening at the cyclic amide bond was explored to demonstrate their potential for further structural elaboration. Methodology for the microwave parallel synthesis of a library from a library is described. The procedure involves the use of an array of expandable reaction vessels, which can accommodate pressure build up within the vessel without loss of volatile solvents or reagents. A 24-membered demonstration library of (1) was generated utilizing our parallel microwave procedures and this library was converted into a further library of (2) and (3) with each library requiring a generation time of sixteen minutes.
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Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster
Division of Organic Chemistry |
