One-pot Two-Step Cycloaddition Reaction for Convenient Synthesis of Polycyclic Spirooxindole-fused [1,3]Oxazines
Jing Sun
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China
Search for more papers by this authorHui Gong
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China
Search for more papers by this authorCorresponding Author
Chaoguo Yan
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, ChinaSearch for more papers by this authorJing Sun
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China
Search for more papers by this authorHui Gong
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China
Search for more papers by this authorCorresponding Author
Chaoguo Yan
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, ChinaSearch for more papers by this authorAbstract
The novel spirooxindoline fused [1,3]oxazines were efficiently synthesized from Diels-Alder reaction of N-arylmaleimides with 1,2-dihydro-2-oxospiro[3H-indole-3,2′-[2H,9aH-pyrido[2,1-b][1,3]oxazines], which were generated in situ from three-component reactions of substituted pyridines and isatins with methyl propiolate, or dimethyl acetylenedicarboxylate. The stereochemistry of the products was clearly clarified by the analysis of 1H NMR data and single crystal structures of the obtained polycyclic compounds.
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REFERENCES
- 1 Singh, G. S.; Desta, Z. Y.. Chem. Rev., 2012, 112, 6104.
- 2 Ball-Jones, N. R.; Badillo, J. J.; Franz, A. K.. Org. Biomol. Chem., 2012, 10, 5165.
- 3 Hong, L.; Wang, R.. Adv. Synth. Catal., 2013, 355, 1023.
- 4 Liu, Y. Y.; Wang, H.; Wan, J. P.. Asian J. Org. Chem., 2013, 2, 374.
- 5 Cao, Z. Y.; Wang, Y. H.; Zeng, X. P.; Zhou, J.. Tetrahedron, 2014, 70, 2406.
- 6 Cheng, D. Q.; Ishihara, Y.; Tan, B.; Barbas, C. B.III. ACS Catal., 2014, 4, 743.
- 7 Zhu, S. L.; Jia, S. J.; Zhang, Y.. Tetrahedron, 2007, 63, 9365.
- 8 Redkin, R. G.; Shemchuk, L. A.; Chernykh, V. P.; Shishkin, O. V.; Shishkina, S. V.. Tetrahedron, 2007, 63, 11444.
- 9 Zhou, F.; Liu, Y. L.; Zhou, J.. Adv. Synth. Catal., 2010, 352, 1381.
- 10 Fang, H. B.; Jin, L.; Huang, N. Y.; Wang, J. Z.; Zou, K.; Luo, Z. G.. Chin. J. Chem., 2013, 31, 831.
- 11 Zhai, J. J.; Gu, C. H.; Jiang, J. N.; Zhang, S. L.; Liao, D. H.; Wang, L.; Zhu, D. R.; Ji, Y. F.. Chin. J. Chem., 2013, 31, 1526.
- 12 Li, M. M.; Xing, P.; Huang, Z. G.; Jiang, B.. Chin. J. Chem., 2013, 31, 49.
- 13 Lo, M. M. C.; Neumann, C. S.; Nagayama, S.; Perlstein, E. O.; Schreiber, S. L.. J. Am. Chem. Soc., 2004, 126, 16077.
- 14 Galliford, C. V.; Scheidt, K. A.. Angew. Chem., Int. Ed., 2007, 46, 8748.
- 15 Chen, X.; Wei, Q.; Luo, S.; Xiao, H.; Gong, L.. J. Am. Chem. Soc., 2009, 131, 13819.
- 16 Eberle, M. K.; Kahle, G. G.; Shapiro, M. J.. J. Org. Chem., 1982, 47, 2210.
- 17 Wei, Q.; Gong, L. Z.. Org. Lett., 2010, 12, 1008.
- 18 Jiang, K.; Jia, Z. J.; Yin, X.; Wu, L.; Chen, Y. C.. Org. Lett., 2010, 12, 2766.
- 19 Lan, Y. B.; Zhao, H.; Liu, Z. M.; Liu, G. G.; Tao, J. C.; Wang, X. W.. Org. Lett., 2011, 13, 4866.
- 20 Tan, B.; Candeias, N. R.; Barbas, C. F.III. J. Am. Chem. Soc., 2011, 133, 4672.
- 21 Albertshofer, K.; Tan, B.; Barbas, C. F.III. Org. Lett., 2012, 14, 1832.
- 22 Pesciaioli, F.; Righi, P.; Mazzanti, A.; Bartoli, G.; Bencivenni, G.. Chem. Eur. J., 2011, 17, 2842.
- 23 Bencivenni, G.; Wu, L. Y.; Mazzanti, A.; Giannichi, B.; Pesciaoli, F.; Song, M. P.; Bartoli, G.; Melchiorre, P.. Angew. Chem., Int. Ed., 2009, 48, 7200.
- 24 Cao, Y. M.; Jiang, X. X.; Liu, L. P.; Shen, F. F.; Zhang, R. T.; Wang, R.. Angew. Chem., Int. Ed., 2011, 50, 9124.
- 25 Tan, B.; Candeias, N. R.; Barbas, C. F.III. Nat. Chem., 2011, 3, 473.
- 26 Wang, L. L.; Peng, L.; Bai, J. F.; Jia, L. N.; Luo, X. Y.; Huang, Q. C.; Xu, X. U.; Wang, L. X.. Chem. Commun., 2011, 47, 5593.
- 27 Reddy, B. V. S.; Rajasekaran, T.; Karthik, G.; Rao, T. P.. Tetrahedron Lett., 2012, 53, 3416.
- 28 Sun, J.; Sun, Y.; Gao, H.; Yan, C. G.. Eur. J. Org. Chem., 2012, 1976.
- 29 Sun, J.; Wu, Q.; Zhang, L. J.; Yan, C. G.. Chin. J. Chem., 2012, 30, 1548.
- 30 Han, Y.; Wu, Q.; Sun, J.; Yan, C. G.. Tetrahedron, 2012, 68, 8539.
- 31 Zhang, L. L.; Sun, J.; Yan, C. G.. Chin. J. Chem., 2013, 31, 1546.
- 32 Liu, Z. M.; Zhang, L. L.; Sun, J.; Yan, C. G.. Chin. J. Chem., 2013, 31, 479.
- 33 Sun, Y.; Sun, J.; Yan, C. G.. Beilstein J. Org. Chem., 2013, 9, 8.
- 34 Zhang, L. J.; Wu, Q.; Sun, J.; Yan, C. G.. Beilstein J. Org. Chem., 2013, 9, 846.
- 35 Fu, Q.; Yan, C. G.. Beilstein J. Org. Chem., 2013, 9, 918.
- 36 Sun, J.; Xie, Y. J.; Yan, C. G.. J. Org. Chem., 2013, 78, 8354.
- 37 Sun, J.; Shen, G. L.; Xie, Y. J.; Yan, C. G.. Chin. J. Chem., 2014, 32, 1143.
- 38 Gao, H.; Sun, J.; Yan, C. G.. J. Org. Chem., 2014, 79, 4131.
- 39 Gao, H.; Sun, J.; Yan, C. G.. Synthesis, 2014, 46, 489.
- 40 Han, Y.; Sheng, Y. J.; Yan, C. G.. Org. Lett., 2014, 14, 5172.
- 41 Sun, J.; Sun, Y.; Gong, H.; Xie, Y. J.; Yan, C. G.. Org. Lett., 2012, 14, 5172.
- 42 Sun, J.; Zhu, D.; Gong, H.; Yan, C. G.. Tetrahedron, 2013, 69, 10565.
- 43 Sun, J.; Sun, Y.; Gong, H.; Yan, C. G.. Mol. Divers., 2013, 17, 627.
- 44 Sun, J.; Gong, H.; Yan, C. G.. Tetrahedron, 2013, 69, 10235.
- 45 Gong, H.; Sun, J.; Yan, C. G.. Tetrahedron, 2014, 70, 6641.
- 46 Nair, V.; Sreekanth, A. R.; Abhilash, N.; Biju, A. T.; Devi, B. R.; Menon, R. S.; Rath, N. P.; Srinivas, R.. Synthesis, 2003, 1895.
- 47 Adib, M.; Yavari, H.; Mollahosseini, M.. Tetrahedron Lett., 2004, 45, 1803.
- 48 Teimouri, M. B.; Abbasi, T.; Ahmadian, S.; Heravi, M. R. P.; Bazhrang, R.. Tetrahedron, 2009, 65, 8120.
- 49 Yavari, I.; Mirzaei, A.; Hossaini, Z.. Mol. Divers., 2010, 14, 343.
- 50 Yang, H. B.; Guan, X. Y.; Wei, Y.; Shi, M.. Eur. J. Org. Chem., 2012, 2792.
