Publication: Azirine/Oxindole ring enlargement via Amidinium intermediates
Azirine/Oxindole ring enlargement via Amidinium intermediates
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Mekhael, M. K. G., Bienz, S., Linden, A., & Heimgartner, H. (2004). Azirine/Oxindole ring enlargement via Amidinium intermediates. Helvetica Chimica Acta, 87(9), 2385–2404. https://doi.org/10.1002/hlca.200490216
Abstract
Abstract
Abstract
A novel general method for the synthesis of oxindoles, namely the 'azirine/oxindole ring enlargement via amidinium-intermediates' has been established: the reaction of 2H-azirin-3-amines 1 with BF3.OEt2 in THF solution at -78° leads to 1,3,3-trialkyl-2-amino-3H-indolium tetrafluoroborates 14 in good yields (Scheme 5). Treatment of aqueous solutions of 14 at 0° with aqueous NaOH (30%) and extraction with CH2Cl2 gives oily substances that are either hydrates of 1,3,3-trialkyl-2-dihydroindol-2-imines 15 or the corresponding indolium hydr
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- Mekhael, Maged K G
- Bienz, Stefan
- Heimgartner, Heinz
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Citations
Mekhael, M. K. G., Bienz, S., Linden, A., & Heimgartner, H. (2004). Azirine/Oxindole ring enlargement via Amidinium intermediates. Helvetica Chimica Acta, 87(9), 2385–2404. https://doi.org/10.1002/hlca.200490216
