Claisen-Schmidt Condensation Involved with C—C Bond Cleavage
- Corresponding author: Yang Yong-Qing, yqy@ujs.edu.cn
Citation:
Yang Yong-Qing, Zhu Meng-Nan, Lu Zheng, Chen Li-Ting, Su Jing. Claisen-Schmidt Condensation Involved with C—C Bond Cleavage[J]. Chinese Journal of Organic Chemistry,
;2016, 36(5): 1073-1079.
doi:
10.6023/cjoc201509040
Mahapatra, D. K.; Asati, V.; Bharti, S. Eur. J. Med. Chem. 2015, 92, 839. (b) Avupati, V. R.; Yejella, R. P. J. Pharm. Pharm. Sci. 2014, 3, 1713.
Umezawa, T.; Seino, T.; Matsuda, F. Org. Lett. 2012, 14, 4206. (b) El-Batta, A.; Jiang, C.; Zhao, W.; Anness, R.; Cooksy, A. L.; Bergdahl, M. J. Org. Chem., 2007, 72, 5244.
Ma, X.-T.; Wang, Y.; Dai, R.-H.; Liu, C.-R.; Tian, S.-K. J. Org. Chem. 2013, 78, 11071. (b) Kwon, M. S.; Kim, N.; Seo, S. H.; Park, I. S.; Cheedrala, R. K.; Park, J. Angew. Chem., Int. Ed. 2005, 42, 6913. (c) Rhee, J. U.; Krishe, M. J. Org. Lett. 2005, 7, 2493.
Wang, Z.; Yin, G.; Qin, J.; Gao, M.; Cao, L.; Wu, A. Synthesis 2008, 3565. (b) Qiu, R.; Qiu, Y.; Meng, Z.; Song, X.; Jia, Z.; Yu, K.; Yin, S. Adv. Mater. Phys. Chem. 2012, 2, 142. (c) Erkkilä, A.; Pinko, P. M. J. Org. Chem. 2006, 71, 2538. (d) Rueping, M.; Bootwicha, T.; Baars, H.; Sugiono, E. Beilstein J. Org. Chem. 2011, 7, 1680. (e) Li, Y.; Chen, D. Chin. J. Chem. 2011, 29, 2086. (f) Yanagisawa, A.; Goudu, R.; Arai, T. Org. Lett. 2004, 6, 4281. (g) Zhang, X.; Feng, X.; Liu, H.; Qin, Y.; Dai, Y. Chin. J. Catal. 2012, 33, 523.
Claisen, L.; Claparède, A. Ber. Dtsch. Chem. Ges. 1881, 14, 2460. (b) Schmidt, J. G. Ber. Dtsch. Chem. Ges. 1881, 14, 1459.
Manojveer, S.; Balamurugan, R. Org. Lett. 2015, 17, 3600. (b) Passalacqua, T. G.; Dutra, L. A.; de Almeida, L.; Velasquez. A. M. A.; Torres, F. A. E.; Yamasaki, P. R.; dos Santos, M. B.; Regasini, L. O.; Michels, P. A. M.; Bolzani, V. D. Bioorg. Med. Chem. Lett. 2015, 25, 3342. (c) Rayar, A.; Veitía, M. S.-I.; Ferroud, C. SpringerPlus 2015, 4, 221. (d) Amin, K. M.; Abou-Seri, S. M.; Awadallah, F. M.; Eissa, A. A. M.; Hassan, G. S.; Abdulla, M. M.; Eur. J. Med. Chem. 2015, 90, 221.
Shoji, M.; Nakagawa, K.; Watanabe, A.; Tsuduki, T.; Yamada, T.; Kuwahara, S.; Kimura, F.; Myyazawa, T. Food Chem. 2014, 151, 126. (b) Vnallinou, N. G.; Evagelopoulos, A.; Schizas, N.; Kazazis, C. Anticancer Res. 2015, 35, 645. (c) Hasima, N.; Aggarwal, B. B. Curr. Med. Chem. 2014, 21, 1583.
Lin, L.; Hutzen, B.; Zuo, M.; Ball, S.; Deangelis, S.; Foust, E.; Pandit, B.; Ihnat, M. A.; Shenoy, S. S.; Kulp, S.; Li, P.-K.; Li, C.; Fuchs, J.; Lin, J. Cancer Res. 2010, 70, 2445. (b) Li, P.-K.; Li, C.; Lin, J.; Fuchs, J. R. WO 2010/121007, 2010[Chem. Abstr. 2010, 153, 546757]. (c) Bill, M. A.; Nicholas, C.; Mace, T. A.; Etter, J. P.; Li, C; Schwartz, E. B.; Fuchs, J. R.; Young, G. S.; Lin, L.; Lin, J.; He, L.; Phelps, M.; Li, P.-K.; Lesinski, G. B. PloS One 2012, 7, e40724.
Mai, A.; Cheng, D.; Bedford, M. T.; Vlaente, S.; Nebbioso, A.; Perrone, A.; Brosch, G.; Sbardella, G.; De Bellis, F.; Miceli, M.; Altucci, L. J. Med. Chem. 2008, 51, 2279.
Leow, P.-C.; Bahety, P.; Boon. C. P.; Lee, C. Y.; Tan, K. L.; Yang, T.; Ee, P.-L. R. Eur. J. Med. Chem. 2014, 71, 67.
The general work up procedure is: Ethyl acetate extract after acidification with dilute hydrochloride followed with water, sodium bicarbonate, and brine wash. The combined organic phase was dried and then concentrated to afford a residue for flash chromatography. In this procedure, acidic material would be removed by sodium bicarbonate wash. In these entries, the sodium bicarbonate wash step was skipped. The residue was dissolved in dichloromethane (2 mL), and then solid insoluble was washed with dichloromethane (0.5 mL×2). The solid was characterized as cinnamic acids 10a, 10c and 10d.
Ameen, D.; Snape, T. J. Tetrahedron Lett. 2015, 56, 1816. (b) Zheng, W.; Wang, Y.; Bai, C.; Wen, J.; Wang, N. Chin. J. Chem. 2015, 33, 401. (c) Peshkov, A. A.; Peshkov, V. A.; Li, Z.; Pereshivko, O. P.; Van der Eycken, E. V. Eur. J. Org. Chem. 2014, 6390. (d) Xie, F.; Yan, F.; Chen, M.; Zheng, M. RSC Adv. 2014, 4, 29502. (e) Maji, T.; Tunge, J. A. Org. Lett. 2014, 16, 5072. (f) Roudier, M.; Constantieux, T.; Quintard, A.; Rodriguez, J. Org. Lett. 2014, 16, 2802. (g) Maji, T.; Ramakumar, K. Tunge, J. A. Chem. Commun. 2014, 50, 14045. (h) Zhou, Y.; Yang, D.; Luo, G.; Luo, Y.; Xue, N.; Qu, J. Tetrahedron 2014, 70, 4668. (i) Yang, D.; Zhou, Y.; Xue, N.; Qau, J. J. Org. Chem. 2013, 78, 4171.
Muthusamy, S.; Gnanaprakasam, B. Tetrahedron Lett. 2005, 46, 635. (b) Gerken, J. B.; Wang, S. C.; Preciado, A. B.; Park, Y. S.; Nishiguchi, G.; Tantillo, D. J.; Little, R. D. J. Org. Chem. 2005, 70, 4598.
Coveney, D. J.; Patel, V. F.; Pattenden, G.; Thompson, D. M. J. Chem. Soc., Perkin Trans. 1 1990, 2721.
Wang, D.; Zhang, Y.; Harris, A.; Gautam, L. N. S.; Chen, Y.; Shi, X. Adv. Synth. Catal. 2011, 353, 2584.
Basaif, S. A.; Sobahi, T. R. J. King Abdulaziz Univ.: Sci. 2005, 17, 107.
Suresh; Kumar, D.; Sandhu, J. S. Synth. Commun. 2010, 40, 1915.
Ghorai, P.; Kraus, A.; Keller, M.; Götte, C.; Igel, P.; Schneider, E.; Schnell, D.; Bernhardt, G.; Dove, S.; Zabel, M.; Elz, S.; Seifert, R.; Bushauer, A. J. Med. Chem. 2008, 51, 7193.
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