Remember Me
Or use your Academic/Social account:


Or use your Academic/Social account:


You have just completed your registration at OpenAire.

Before you can login to the site, you will need to activate your account. An e-mail will be sent to you with the proper instructions.


Please note that this site is currently undergoing Beta testing.
Any new content you create is not guaranteed to be present to the final version of the site upon release.

Thank you for your patience,
OpenAire Dev Team.

Close This Message


Verify Password:
Verify E-mail:
*All Fields Are Required.
Please Verify You Are Human:
fbtwitterlinkedinvimeoflicker grey 14rssslideshare1
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!

    • Lett., 2010, 12, 3844; (b) Z. Shi, Y. Cui, N. Jiao, Org. Lett., 2010, 12, 2908; (c) C. C. Silveira, S. R. Mendes, L. Wolf, G. M. Martins, Tetrahedron Lett., 2010, 51, 4560; (d) M. Bandini, A. Eichholzer, Angew. Chem. Int. Ed., 2009, 48, 9608; (e) M. Yamashita, H.
    • Horiguchi, K. Hirano, T. Satoh, M. Miura, J. Org. Chem., 2009, 74, 7481; (f) G. R. Humphrey, J. T. Kuethe, Chem. Rev., 2006, 106, 2875.
    • 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.
    • Iwabuchi, Org. Lett., 2004, 6, 4303.
    • Org. Chem., 2007, 72, 2978. For other examples, see: (b) T. Lindel, L. Bräuchle, G. Golz, P. Böhrer, Org. Lett., 2007, 9, 283. (c) M.
    • Lachia, C. Poriel, A. M. Z. Slawin, C. J. Moody, Chem. Commun., 2007, 286; (d) M. Pettersson, D. Knueppel, S. F. Martin, Org. Lett., 2007, 9, 4623; (e) P. S. Baran, J. M. Richter, J. Am. Chem. Soc., 2005, 127, 15394; (f) M. Ito, C. W. Clark, M. Mortimore, J. B. Goh, S. F. Martin, J. Am. Chem. Soc., 2001, 123, 8003; (g) X. Zhang, C. S.
    • Foote, J. Am. Chem. Soc., 1993, 115, 8867; (h) D. V. C. Awang, A.
    • Vincent, D. Kindack, Can. J. Chem., 1984, 62, 2667; (i) A. Walser, J.
    • F. Blount, R. I. Fryer, J. Org. Chem., 1973, 38, 3077; (j) R. M.
    • Acheson, R. W. Snaith, J. M. Vernon, J. Chem. Soc., 1964, 3229; (k) N. Finch, W. I. Taylor, J. Am. Chem. Soc., 1962, 84, 3871.
    • 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.
    • Pharm., 1992, 325, 353.
    • 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.
  • No related research data.
  • No similar publications.

Share - Bookmark

Cite this article