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Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 6: 1177 - 1182

DOI: https://doi.org/10.6023/cjoc201308020

Articles

Organic Base Catalyzed Cascade Phospho-Aldol-Brook Rearrangement Reaction of Isatins with H-phosphonates

  • Fang Wei ,
  • Liu Guogui ,
  • Huang Xiaofei ,
  • Jia Jun ,
  • Wang Xingwang
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  • a. Analysis and Testing Center, Soochow University, Suzhou 215123;
    b. College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123

Received date: 2013-08-16

  Revised date: 2013-12-18

  Online published: 2014-02-12

Supported by

Project supported by the National Natural Science Foundation of China (No. 21272166) and the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (No. 13KJA150004).

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Abstract

A cascade phospho-aldol-Brook rearrangement reaction of isatins with H-phosphonates was reported by the use of the organic base, such as 1,1,3,3-tetramethylguanidine (TMG) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), as an organocatalyst. Two series of 2-oxoindolin-3-yl phosphates were obtained in good to excellent yields under mild reaction conditions.

Key words： α-oxindole-phosphonates; isatins; H-phosphonates; Brook rearrangement; cascade reaction

Cite this article

Fang Wei , Liu Guogui , Huang Xiaofei , Jia Jun , Wang Xingwang . Organic Base Catalyzed Cascade Phospho-Aldol-Brook Rearrangement Reaction of Isatins with H-phosphonates[J]. Chinese Journal of Organic Chemistry, 2014 , 34(6) : 1177 -1182 . DOI: 10.6023/cjoc201308020

References

[1] Gil-Turnes, M. S.; Hay, M. E.; Fenical, W. Science 1989, 246, 116.
[2] Webber, S. E.; Tikhe, J.; Worland, S. T.; Fuhrman, S. A.; Hendrickson, T. F.; Mathews, D. A.; Love, R. A.; Patick, A. K. J. Med. Chem. 1996, 39, 5072.
[3] Sikorshi, J. A.; Miller, M. J.; Walker, M. C. Phosphorous, Sulfur Silicon Relat. Elem. 1993, 76, 115.
[4] Stowasser, B.; Budt, K. H.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625.
[5] Pompliano, D. L.; Rands, E.; Gibbs, J. B. Biochemistry 1992, 31, 3800.
[6] Wang, J.-G.; Tan, H.-Z.; Li, Y.-H.; Ma, Y.; Li, Z.-M.; Guddat, L. W. J. Agric. Food Chem. 2011, 59, 9892.
[7] Medvedev, A. E.; Goodwin, A.; Clow, A.; Halket, J.; Glover, V.; Sandler, M. Biochem. Pharmacol. 1992, 44, 590.
[8] Zhou, L.; Liu, Ying.; Zhang, W.-L.; Wei, P.; Huang, C.-K.; Pei, J.-F.; Yuan, Y.-X.; Lai, L.-H. J. Med. Chem. 2006, 49, 3440.
[9] Hall, M. D.; Salam, N. K.; Hellawell, J. L.; Fales, H. M.; Kensler, C. B.; Ludwig, J. A.; Szakács, G.; Hibbs, D. E.; Gottesman, M. M. J. Med. Chem. 2009, 52, 3191.
[10] (a) Wynberg, H.; Smaardijk, A. A. Tetrahedron Lett. 1983, 24, 5899.
(b) Wang, F.; Liu, X.; Cui, X.; Xiong, Y.; Zhou, X.; Feng, X. Chem. Eur. J. 2009, 15, 589.
(c) Uraguchi, D.; Ito, T.; Ooi, T. J. Am. Chem. Soc. 2009, 131, 3836.
(d) Uraguchi, D.; Ito, T.; Nakamura, S.; Ooi, T. Chem. Sci. 2010, 1, 488.
[11] (a) Joly G. D.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 4102.
(b) Akiyama, T.; Morita, H.; Itoh, J.; Fuchibe, K. Org. Lett. 2005, 7, 2583.
(c) Pettersen, D.; Marcolini, M.; Bernardi, L.; Fini, F.; Herrera, R. P.; Sgarzani, V.; Ricci, A. J. Org. Chem. 2006, 71, 6269.
(d) Cheng, X.; Goddard, R.; Buth, G.; List, B. Angew. Chem., Int. Ed. 2008, 47, 5079.
(e) Nakamura, S.; Hayashi, M.; Hiramatsu, Y.; Shibata, N.; Funahashi, Y.; Toru, T. J. Am. Chem. Soc. 2009, 131, 18240.
[12] (a) Bartoli, G.; Bosco, M.; Carlone, A.; Locatelli, M.; Mazzanti, A.; Sambri, L.; Melchiorre, P. Chem. Commun. 2007, 722.
(b) Carlone, A.; Bartoli, G.; Bosco, M.; Sambri, L.; Melchiorre, P. Angew. Chem., Int. Ed. 2007, 46, 4504.
(c) Ibrahem, I.; Rios, R.; Vesely, J.; Hammar, P.; Eriksson, L.; Himo, F.; Córdova, A. Angew. Chem., Int. Ed. 2007, 46, 4507.
(d) Fu, X.; Jiang, Z.; Tan, C.-H. Chem. Commun. 2007, 5058.
(e) Maerten, E.; Cabrera, S.; Jørgensen, K. A. J. Org. Chem. 2007, 72, 8893.
(f) Terada, M.; Ikehara, T.; Ube, H. J. Am. Chem. Soc. 2007, 129, 14112.
(g) Wang, J.; Heikkinen, L. D.; Li, H.; Zu, L.; Jiang, W.; Xie, H.; Wang, W. Adv. Synth. Catal. 2007, 349, 1052;
(h) Zhu, Y.; Malerich, J. P.; Rawal, V. H. Angew. Chem., Int. Ed. 2010, 49, 153.
(i) Wen, S.; Li, P.; Wu, H.; Yu, F.; Liang, X.; Ye, J. Chem. Commun. 2010, 46, 4806.
[13] Hall, M. D.; Brimacombe, K. R.; Varonka, M. S.; Pluchino, K. M.; Monda, J. K.; Li, J.-Y.; Walsh, M. J.; Boxer, M. B.; Warren, T. H.; Fales, H. M.; Gottesman, M. M. J. Med. Chem. 2011, 54, 5878.
[14] (a) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945.
(b) Bignan, G. C.; Battista, K.; Connolly, P. J.; Orsini, M. J.; Liu, J. C.; Middleton, S. A.; Reitz, A. B. Bioorg. Med. Chem. Lett. 2005, 15, 5022.
[15] (a) Shankar, J.; Karnakar, K.; Srinivas, B.; Nageswar, Y. V. D. Tetrahedron Lett. 2010, 51, 3938.
(b) Peng, L.; Wang, L.-L.; Bai, J.-F.; Jia, L.-N.; Yang, Q.-C. Huang, Q.-C.; Xu, X.-Y.; Wang, L.-X. Tetrahedron Lett. 2011, 52, 6207.
[16] Hayashi, M.; Nakamura, S. Angew. Chem., Int. Ed. 2011, 50, 2249.
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