Chinese Journal of Organic Chemistry >
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.
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.
Feng Jun, Ablajan Keyume, Ma Xiabing, Li Wenbo, Obul Mamateli . Multi-Component One-Pot Reactions for the Synthesis ofSpirooxindole-pyrano[2,3-c]pyrazole Derivatives[J]. Chinese Journal of Organic Chemistry, 2016 , 36(1) : 222 -228 . DOI: 10.6023/cjoc201507011
[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.
/
| 〈 |
|
〉 |
