Abstract
Ketone–ketone cross-aldol reaction of isatins and unactivated ketones was catalyzed by glucose-containing imidazolium salt β-1-imidazole-2,3,4,6-tetra-o-hydroxy-d-glucopyranosyl bromide in neutral condition to generate 3-alkyl-3-hydroxyindolin-2-ones in excellent yield.
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References
H. Pellissier, Tetrahedron 63 (2007)
B. List, Acc. Chem. Res. 37 (2004)
W. Notz, F. Tanaka, C.F. Barbas III, Acc. Chem. Res. 37 (2004)
B. List, Tetrahedron 58 (2002)
B. List, R.A. Lerner, C.F. Barbas III, J. Am. Chem. Soc. 122 (2000)
T. Kano, R. Sakamoto, K. Maruoka, Org. Lett. 16 (2014)
F. Sladojevich, A. Trabocchi, A. Guarna, D.J. Dixon, J. Am. Chem. Soc. 133 (2011)
J.Y. Li, N.K. Fu, X. Li, S.Z. Luo, J.P. Cheng, J. Org. Chem. 75 (2010)
V. Malkov, A. Kabeshov, M. Bella, O. Kysilka, A. Malyshev, K. Pluháêkova, P. Koêvsky, Org. Lett. 9 (2007)
W.B. Chen, X.L. Du, L.F. Cun, X.M. Zhang, W.C. Yuan, Tetrahedron 66 (2010)
W.B. Chen, Y.H. Liao, X.L. Du, X.M. Zhang, W.C. Yuan, Green Chem. 11 (2009)
F. Xue, S. Zhang, L. Liu, W. Duan, W. Wang, Chem. Asian J. 4 (2009)
B. Zhu, W. Zhang, R. Lee, Z.Q. Han, W.G. Yang, D. Tan, K.W. Huang, Z.Y. Jiang, Angew. Chem. Int. Ed. 125 (2013)
P. Satyamaheshwar, Curr. Bioact. Compd. 5 (2009)
M. Kitajima, I. Mori, K. Arai, N. Kogure, H. Takayama, Tetrahedron Lett. 47 (2006)
G. Luppi, P.G. Cozzi, M. Monari, B. Kaptein, Q.B. Broxterman, C. Tomasini, J. Org. Chem. 70 (2005)
A.J. Pearson, S. Panda, S.D. Bunge, J. Org. Chem. 78 (2013)
R.J. Corrêa, S.J. Garden, G. Angelici, C. Tomasini, Eur. J. Org. Chem. 4 (2008)
T.T. Yan, X.Y. Wang, H.B. Sun, J. Liu, Y.M. Xie, Molecules 18 (2013)
M.A. Kabeshov, O. Kysilka, L. Rulíšek, Y.V. Suleimanov, M. Bella, A.V. Malkov, P. Kočovský, Chem. Eur. J. 21 (2015)
T. Itoh, H. Ishikawa, Y. Hayashi, Org. Lett. 11 (2009)
N. Hara, S. Nakamura, N. Shibata, T. Toru, Adv. Synth. Catal. 352 (2010)
A. Bañón-Caballero, J. Flores-Ferrándiz, G. Guillena, C. Nájera, Molecules 20 (2015)
T.P. Kumar, N. Manjula, K. Katragunta, Tetrahedron Asymmetr. 26 (2015)
J. Kimura, U.V.S. Reddy, Y. Kohari, C. Seki, Y. Mawatari, K. Uwai, Y. Okuyama, E. Kwon, M. Tokiwa, M. Takeshita, T. Iwasa, H. Nakano, Eur. J. Org. Chem. 22 (2016)
P.H. Mohite, P. Drabina, F. Bureš, Synthesis 49 (2016)
G.D. Yadav, S. Singh, Tetrahedron Asymmetr. 27 (2016)
J. Wang, Q. Liu, Q. Hao, Y.H. Sun, Y.M. Luo, H. Yang, Chirality 27 (2015)
J. Guang, Q.S. Guo, J.C.G. Zhao, Org. Lett. 14 (2012)
J.L. Qian, W.B. Yi, X. Huang, J.P. Jasinski, W. Zhang, Adv. Synth. Catal. 358 (2016)
S. Abbarajua, J.C.G. Zhao, Adv. Synth. Catal. 356 (2014)
Q.S. Guo, M. Bhanushali, C.G. Zhao, Angew. Chem. Int. Ed. 49 (2010)
C. Shen, F.Y. Shen, H.J. Xia, P.F. Zhang, X.Z. Chen, Tetrahedron Asymmetr. 22 (2011)
C.W. Suh, C.W. Chang, K.W. Choi, Y.J. Lim, D.Y. Kim, Tetrahedron Lett. 54 (2013)
Y. Liu, P.C. Gao, J.F. Wang, Q. Sun, Z.M. Ge, R.T. Li, Synlett 23 (2012)
H.W. Zhao, W. Meng, Z. Yang, T. Tian, Z.H. Sheng, H.L. Li, X.Q. Song, Y.T. Zhang, S. Yang, B. Li, Chin. J. Chem. 32 (2014)
K.N. Tiwari, D. Bora, G. Chauhan, D. Yadav, K. Sharma, A. Thakur, L. Singh, V. Tripathi, Synth. Commun. 46 (2016)
Q.J. Zhou, Y. Wan, X.X. Zhang, L.Z. Zhang, H. Zou, H. Cui, S.L. Zhou, H.Y. Wang, H. Wu, Tetrahedron 71 (2015)
L.Z. Zhang, Y. Wan, X.X. Zhang, H. Cui, H. Zou, Q.J. Zhou, H. Wu, Tetrahedron Lett. 56 (2015)
R. Yuan, Y.J. Wang, Y. Fang, W.H. Ge, W. Lin, M.Q. Li, J.B. Xu, Y. Wan, Y. Liu, H. Wu, Chem. Eng. J. 316 (2017)
E. Pretsch, P. Buhlmann, C. Affolter, Structure Determination of Organic Compounds Tables of Spectral Data (Springer, Berlin, 2000)
Acknowledgements
We are grateful to the foundation of the Priority Academic Program Development of Jiangsu Higher Education Institutions, Major Project of Natural Science Research of University in Jiangsu (nos. 14KJA430003, 15KJA180002), and Aid project for PhD faculties in Jiangsu Normal University (17XLR023), for financial support.
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Wan, Y., Yuan, R., Cui, H. et al. Glucose-containing imidazolium salt-catalyzed cross-aldol reaction of isatins and unactivated ketones. Res Chem Intermed 44, 2561–2570 (2018). https://doi.org/10.1007/s11164-017-3246-3
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DOI: https://doi.org/10.1007/s11164-017-3246-3