多组分反应合成螺吲哚-吡喃并[2,3-c]吡唑类化合物的研究
收稿日期: 2015-07-15
修回日期: 2015-08-29
网络出版日期: 2015-09-06
基金资助
新疆教育部研究生科研创新项目基金(No. XJGRI2014019)、国家自然科学基金(No. 21462041)和新疆维吾尔自治区天山英才培养计划资助项目.
Multi-Component One-Pot Reactions for the Synthesis ofSpirooxindole-pyrano[2,3-c]pyrazole Derivatives
Received date: 2015-07-15
Revised date: 2015-08-29
Online published: 2015-09-06
Supported by
Project supported by the Graduate Student Research Innovation Project of Xinjiang Educational Department (No. XJGRI2014019), the National Natural Science Foundation of China (No. 21462041), and the Tianshan Talent Cultivation Project of Xinjiang Uyghur Autonomous Region.
报道了一种利用多组分一锅法高效地合成多取代的螺吲哚-吡喃并[2,3-c]吡唑类化合物的方法. 该方法用丁炔二酸酯、肼、靛红和(E)-1-甲硫基-1-甲氨基-2-硝基乙烯作为原料, 在三乙胺的催化下获得了较高的产率. 该方法简单方便, 为该类化合物的合成提供了一个参考依据.
关键词: 螺环吲哚; 多组分反应; 一锅法合成; 吡喃并[2,3-c]吡唑
冯俊, 阿布拉江·克依木, 马夏冰, 李文博, 麦麦提艾力·奥布力 . 多组分反应合成螺吲哚-吡喃并[2,3-c]吡唑类化合物的研究[J]. 有机化学, 2016 , 36(1) : 222 -228 . DOI: 10.6023/cjoc201507011
A highly efficient strategy for the one-pot synthesis of multi-substituted spirooxindol-pyrano[2,3-c]pyrazole derivatives was developed. The product formed in good yield from the reaction of acetylenedicarboxylate, hydrazine, isatin, and (E)-1-methylthio-1-methylamino-2-nitroethylene in the presence of Et3N catalyst. This simple and convenient method could also be used to prepare similar types of product.
[1] (a) Chen, X.-H.; Wei, Q.; Luo, S.-W.; Xiao, H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 13819.(b) Zhang, M.-M.; Zhou, Y. J.; Li, Y. L.; Liu, Y.; Wang, X.-S. Chin. J. Org. Chem. 2013, 33, 1728 (in Chinese).(张梅梅, 周玉静, 李玉玲, 刘 蕴, 王香善, 有机化学, 2013, 33, 1728.)
[2] (a) Tietze, L. F. Chem. Rev. 1996, 96, 115.(b) Christoffers, J. Eur. J. Org. Chem. 1998, 1998, 1259.
[3] (a) Winkler, J. D.; Bowen, C. M.; Michelet, V. J. Am. Chem. Soc. 1998, 120, 3237.(b) Schelkun, R. M.; Yuen, P.-W.; Serpa, K.; Meltzer, L. T.; Wise, L. D.; Whittemore, E. R.; Woodward, R. M. J. Med. Chem. 2000, 43, 1892.
[4] (a) Elinson, M. N.; Dorofeev, A. S.; Miloserdov, F. M.; Nikishin, G. I. Mol. Divers. 2009, 13, 47.(b) Liu, W.-B.; Jiang, H.-F.; Qiao, C.-L. Tetrahedron 2009, 65, 2110.
[5] (a) Tyndall, D. V.; Al Nakib, T.; Meegan, M. J. Tetrahedron Lett. 1988, 29, 2703.(b) Quintela, J.; Peinador, C.; Moreira, M. J. Tetrahedron 1995, 51, 5901.
[6] Kimura, K.; Utsumi, T.; Teranishi, T.; Yokoyama, M.; Sakamoto, H.; Okamoto, M.; Arakawa, R.; Moriguchi, H.; Miyaji, Y. Angew. Chem., Int. Ed. 1997, 36, 2452.
[7] Parreira, R. L.; Abrahão, O. R.; Galembeck, S. E. Tetrahedron 2001, 57, 3243.
[8] Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993.
[9] (a) Li, Y.; Chen, H.; Shi, C.; Shi, D.; Ji, S. J. Comb. Chem. 2010, 12, 231.(b) Zou, Y.; Hu, Y.; Liu, H.; Shi, D. Q. ACS Comb. Sci. 2012, 14, 38.
[10] O'Callaghan, C.; Brian, H.; McMurry, T. J. Chem. Res. 1999, 457.
[11] Zhang, X.-N.; Dong, X.; Wei, Y.; Shi, M. Tetrahedron 2014, 70, 2838.
[12] (a) Edmondson, S.; Danishefsky, S. J.; Sepp-Lorenzino, L.; Rosen, N. J. Am. Chem. Soc. 1999, 121, 2147.(b) Kornet, M. J.; Thio, A. P. J. Med. Chem. 1976, 19, 892.
[13] (a) Hari, G. S.; Lee, Y. R. ChemInform 2010, 41, 453.(b) Karnakar, K.; Narayana Murthy, S.; Ramesh, K.; Harsha Vardhan Reddy, K.; Nageswar, Y. V. D.; Chandrakala, U.; Prabhavathi Devi, B. L. A.; Prasad, R. B. N. Tetrahedron Lett. 2012, 53, 3497.
[14] (a) Brault, L.; Migianu, E.; Néguesque, A.; Battaglia, E.; Bagrel, D.; Kirsch, G. Eur. J. Med. Chem. 2005, 40, 757.(b) Bartoli, G.; Bartolacci, M.; Bosco, M.; Foglia, G.; Giuliani, A.; Marcantoni, E.; Sambri, L.; Torregiani, E. J. Org. Chem. 2003, 68, 4594.(c) Mahboobi, S.; Eibler, E.; Koller, M.; Kumar Kc, S.; Popp, A.; Schollmeyer, D. J. Org. Chem. 1999, 64, 4697.
[15] Wu, H.; Zhang, L.-L.; Tian, Z.-Q.; Huang, Y.-D.; Wang, Y.-M. Chem.-Eur. J. 2013, 19, 1747.
[16] (a) Dandia, A.; Singh, R.; Khaturia, S.; Mérienne, C.; Morgant, G.; Loupy, A. Bioorg. Med. Chem. 2006, 14, 2409.(b) Schulz, V.; Davoust, M.; Lemarié, M.; Lohier, J.-F.; Oliveira Santos, J. S.; Metzner, P.; Brière, J.-F. Org. Lett. 2007, 9, 1745.(c) Shanthi, G.; Subbulakshmi, G.; Perumal, P. T. Tetrahedron 2007, 63, 2057.(d) Wang, L. J.; Keyume, A.; Feng, J. Ultrason. Sonochem. 2015, 22, 113.(e) Xie, W. Q.; Zuo, Z. W.; Zi, W.-W.; Ma, D. W. Chin. J. Org. Chem. 2013, 33, 869 (in Chinese).(谢卫青, 左智伟, 资伟伟, 马大为, 有机化学, 2013, 33, 869.)
[17] (a) Kusebauch, U.; Beck, B.; Messer, K.; Herdtweck, E.; Dömling, A. Org. Lett. 2003, 5, 4021.(b) Zhu, Y.; Huang, S.; Wan, J.; Yan, L.; Pan, Y.; Wu, A. Org. Lett. 2006, 8, 2599.(b) Xiao, L. W.; Peng, X.-X.; Zhou, Q. X.; Kou, W.; Shi, Y. R. Chin. J. Org. Chem. 2015, 35, 1204 (in Chinese).(肖立伟, 彭晓霞, 周秋香, 寇伟, 时亚茹, 有机化学, 2015, 35, 1204.)
[18] (a) Chen, H.; Shi, D. Tetrahedron 2011, 67, 5686.(b) Tang, M.; Xing, D.; Cai, M. Q.; Hu, W. H. Chin. J. Org. Chem. 2014, 34, 1268 (in Chinese).(唐敏, 邢栋, 蔡茂强, 胡文浩, 有机化学, 2014, 34, 1268.)
[19] Zhu, Q.; Jiang, H.; Li, J.; Liu, S.; Xia, C.; Zhang, M. J. Comb. Chem. 2009, 11, 685.
[20] (a) Rajarathinam, B.; Vasuki, G. Org. Lett. 2012, 14, 5204.(b) Cao, S.; Jing, Y. F.; Liu, Y.-Y.; Wan, J. P. Chin. J. Org. Chem. 2014, 34, 876 (in Chinese).(曹硕, 景艳锋, 刘云云, 万结平, 有机化学, 2014, 34, 876.)
[21] Gröger, H. Chem. Rev. 2003, 103, 2795.
[22] Kamalraja, J.; Muralidharan, D.; Paramasivan Thirumalai Perumal, P. T. Synlett 2012, 2894.
[23] Kanchithalaivan, S.; Sivakumar, S.; Ranjith Kumar, R.; Elumalai, P.; Ahmed, Q. N.; Padala, A. K. ACS Comb. Sci. 2013, 15, 631.
[24] Jayabal, K.; Paramasivan, T. P. Tetrahedron Lett. 2014, 55, 2010.
[25] Kamalraja, J.; Perumal, P. T. Tetrahedron Lett. 2014, 55, 3561.
[26] Wang, Y.-L.; Luo, J.; Xing, T.-T.; Liu, Z.-L. Chin. J. Org. Chem. 2013, 33, 2016 (in Chinese).(王英磊, 罗军, 邢昙昙, 刘祖亮, 有机化学, 2013, 33, 2016.)
[27] (a) Feng, J.; Keyume, A.; Sali, A. Tetrahedron 2014, 70, 484.(b) Keyume, A.; Esmayil, Z.; Wang, L. J.; Feng, J. Tetrahedron 2014, 70, 3976.(c) Wang, L. J.; Keyume, A. Curr. Org. Synth. 2014, 11, 310.
[28] (a) Liu, K.; Teng, H.-L.; Wang, C.-J. Org. Lett. 2014, 16, 4508.(b) Mhasni, O.; Rezgui, F. Tetrahedron 2011, 67, 6322.
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