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Moran, Wesley J.; MacRory, Kerry L.; Rodriguez, Arantxa (2012)
Publisher: Royal Society of Chemistry
Languages: English
Types: Article
Subjects: Q1, QD
An unexpected oxidative rearrangement was observed when indoles substituted with 2-hydroxymalonates were subjected to typical iodination conditions. This unusual and unprecedented transformation is successful for a number of derivatives.
  • The results below are discovered through our pilot algorithms. Let us know how we are doing!

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    • For the bromination and chlorination of 1,3-disubstituted indoles, see: S. Tang, J.-H. Li, Y.-X. Xie, N.-X. Wang, Synthesis, 2007, 1535.
    • (a) J.-M. Vatèle, Tetrahedron, 2010, 66, 904. For other recent examples, see: (b) M. Uyanik, R. Fukatsu, K. Ishihara, Org. Lett., 2009, 11, 3470; (c) M. Shibuya, S. Ito, M. Takahashi, Y. Iwabuchi, Org. Lett., 2008, 10, 4715; (d) M. Shibuya, S. Ito, M. Takahashi, Y.
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    • 1-Methylindole and some 1-methyl-2-vinylindoles are known to react with diethyl ketomalonate: (a) U. Pindur, M.-H. Kim, Tetrahedron, 1989, 45, 6427; (b) U. Pindur, M.-H. Kim, Arch.
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    • Other Lewis acids have been reported to promote double addition of indoles to diethyl ketomalonate or to mediate indole dimerization: see ref. 6a.
    • Typical experimental procedure: Iodine (83 mg, 0.328 mmol) in dry THF (0.90 mL) was added via cannula to silver trifluoroacetate (87 mg, 0.393 mmol) and diethyl 2-hydroxy-2-(1-methyl-1H-indol-3- yl)malonate 1a (100 mg, 0.328 mmol) in dry THF (1.8 mL). The reaction mixure was stirred at room temperature for 16 hours under a nitrogen atmosphere and then quenched with saturated sodium thiosulfate and extracted with EtOAc. The organic layer was dried over MgSO4, concentrated and purified by flash chromatography on silica gel (5:1 petroleum ether/ethyl acetate) to provide diethyl 2-(1- methyl-2-oxoindolin-3-ylidene)malonate 2a as a red solid (61 mg, 61%).
    • CCDC 828908 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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