Rearrangement in the reaction of oxindole with o-nitrobenzyl chloride |
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| Authors: | V. Dave E.W. Warnhoff |
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| Affiliation: | Department of Chemistry, University of Western Ontario, London, Canada N6A 5B7 |
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| Abstract: | The alkylation of oxindole with o-nitrobenzyl chloride produces three products, 5a, 6, and 10. The N-hydroxyindoloquinolone 5a probably arises by rearrangement of an initial alkylation product as shown in Scheme 1. The indoloquinolone 6 is formed by base-catalyzed elimination of o-nitrobenzaldehyde from the dialkylation product 10 and also apparently by a thermal process most simply considered as a 1,5-sigmatropic rearrangement of 10 → 12. |
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