A novel method for the generation of nitrile oxides on solid phase: application to the synthesis of substituted benzopyranoisoxazoles |
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| Authors: | Chao Esther Y Minick Douglas J Sternbach Daniel D Shearer Barry G Collins Jon L |
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| Affiliation: | GlaxoSmithKline, Five Moore Drive, Research Triangle Park, NC 27709, USA. |
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| Abstract: | A solid-phase synthesis of substituted benzopyranoisoxazoles is described. The six-step synthesis features a novel method of generating nitrile oxides on a polymer support followed by an intramolecular 1,3-dipolar cycloaddition with a tethered alkyne for assembly of the benzopyranoisoxazole scaffold. Furthermore, the utilization of single-bead attenuated total reflectance Fourier transform infrared (ATR-IR) microspectroscopy as an essential analytical tool for reaction optimization is highlighted. |
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