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Synthesis of SF5-containing benzisoxazoles, quinolines, and quinazolines by the Davis reaction of nitro-(pentafluorosulfanyl)benzenes
Petr Beier and Tereza Pastýříková
Beilstein J. Org. Chem. 2013, 9, 411–416.
https://doi.org/10.3762/bjoc.9.43
How to Cite
Beier, P.; Pastýříková, T. Beilstein J. Org. Chem. 2013, 9, 411–416. doi:10.3762/bjoc.9.43
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- Kanishchev, O. S.; Dolbier, W. R. SF5-Substituted Aromatic Heterocycles. Advances in Heterocyclic Chemistry 2016, 120, 1–42. doi:10.1016/bs.aihch.2016.03.008
- Wiȩcław, M.; Bobin, M.; Kwast, A.; Bujok, R.; Wróbel, Z.; Wojciechowski, K. General synthesis of 2,1-benzisoxazoles (anthranils) from nitroarenes and benzylic C–H acids in aprotic media promoted by combination of strong bases and silylating agents. Molecular diversity 2015, 19, 807–816. doi:10.1007/s11030-015-9627-x
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