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- W2488124893 abstract "This chapter shows that aryl azides, like aryl nitro compounds, can form aryl nitrenes, or nitrene equivalents, under suitable conditions, leading to indoles. Sundberg is most appropriately associated with the pyrolysis of aryl azides to form indoles. The first synthesis of 2-nitroindole was reported by Pelkey and Gribble via a Sundberg reaction (Entry 6). Similarly, 5,6-dimethoxy-2-nitroindole was prepared in 45% yield. The synthesis of 4,6-dinitroindole (Entry 7) began with 2,4,6-trinitrostyrene and sodium azide followed by in situ thermolysis of the 2-azido-4,6-dinitrostyrene. A double Sundberg synthesis was employed to prepare the indole in Entry 8. The reaction in Entry 9 also afforded an isonitrile (4-isocyano-1-(2-TIPS-1H-pyrrol- 3-yl)but-2-enenitrile, 20% yield), and a similar reaction with 3-azido-4-(thien-3-yl)pyridine gave pyrido[3,4-b] thienopyrrole in 29% yield." @default.
- W2488124893 created "2016-08-23" @default.
- W2488124893 creator A5049245360 @default.
- W2488124893 date "2016-06-17" @default.
- W2488124893 modified "2023-09-23" @default.
- W2488124893 title "Sundberg Indole Synthesis" @default.
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- W2488124893 doi "https://doi.org/10.1002/9781118695692.ch27" @default.
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