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Solid-phase synthesis of quinoxaline, thiazine, and oxazine analogs through a benzyne intermediate
- Source :
- Tetrahedron Letters. 46:7443-7446
- Publication Year :
- 2005
- Publisher :
- Elsevier BV, 2005.
-
Abstract
- A solid-phase synthetic route to quinoxaline, thiazine, and oxazine analogs is described. N-Alloc-3-amino-3-(2,4-difluoro-5-nitrophenyl)propanoic acid was tethered to Rink resin via its carboxylic acid group. The 4-arylfluorine was displaced with a primary amine, alcohol, or thiol to create, respectively, a resin bound aniline, phenol, or thiophenol derivative with one diversity element and one single atom (e.g., N, S, or O) diversity point. A fused heterocyclic system was subsequently created via a benzyne heterocyclization initiated by dehydrofluorination with strong base. Acid treatment released the desired products in high yield and moderate purity.
Details
- ISSN :
- 00404039
- Volume :
- 46
- Database :
- OpenAIRE
- Journal :
- Tetrahedron Letters
- Accession number :
- edsair.doi...........bdb5fee07f9b5f31b622f22ecd71cadc