Iodine Promoted Synthesis of Pyrano[3, 2-c]quinoline-4, 5-diones
- Corresponding author: Wang Daolin, wangdaolin@sina.com
Citation:
Zhou Ting, Wang Daolin, Qian Jianhua, Zhao Wei. Iodine Promoted Synthesis of Pyrano[3, 2-c]quinoline-4, 5-diones[J]. Chinese Journal of Organic Chemistry,
;2017, 37(6): 1548-1555.
doi:
10.6023/cjoc201612001
(a) Chen, J. J.; Chen, P. H.; Liao, C. H.; Huang S. Y.; Chen, I. S. J. Nat. Prod. 2007, 70, 1444.
(b) Hanawa, F.; Fokialakis N.; Skaltsounis, A. L. Planta Med. 2004, 70, 531.
(c) Madkour, H. M. F.; Mahmoud, M. R.; Sakr, A. M.; Habasy, M. M. Sci. Pharm. 2001, 69, 33.
Chen, I. S.; Wu, S. J.; Tsai, I. L.; Wu, T. S.; Pezzuto, J. M.; Lu, M. C.; Chai, H.; Suh N.; Teng, C. M. J. Nat. Prod. 1994, 57, 1206.
doi: 10.1021/np50111a003
(a) Barr, S. A.; Neville, C. F.; Grundon, M. F.; Boyd, D. R.; Malone, J. F.; Evans, T. A. J. Chem. Soc. Perkin Trans. 1 1995, 445.
(b) Ngadjui, B. T.; Ayafor, J. F.; Bilon, A. E. N.; Sondengam, B. L.; Connolly J. D.; Rycroft, D. S. Tetrahedron, 1992, 48, 8711.
(c) Grundon, M. F. Tetrahedron, 1978, 34, 143.
Ghorab, M. M.; Heiba, H. I.; Amin, N. E. Pharmazie 1999, 54, 226.
Tavares, L. C.; Johann, S.; Alves, T. M. A.; Guerra, J. C.; Souza-Fagundes, E. M.; Cisalpino, P. Silva.; Bortoluzzi, A. J.; Caramori, G. F.; Piccoli. R. M.; Braibante, H. T. S.; Braibante, M. E. F.; Pizzolatti, M. G. Eur. J. Med. Chem. 2011, 46, 4448.
doi: 10.1016/j.ejmech.2011.07.019
Guo, R. H.; Zhang, Q.; Ma, Y. B.; Luo, J.; Geng, C. A.; Wang, L. J.; Zhang, X. M.; Zhou, J.; Jiang, Z. Y.; Chen. J. J. Eur. J. Med. Chem. 2011, 46, 307.
doi: 10.1016/j.ejmech.2010.11.019
Curreli, F.; Zhang, H.; Zhang, X.; Pyatkin, I.; Victor, Z.; Altieri, A.; Debnath, A. K. Bioorg. Med. Chem. 2011, 19, 77.
doi: 10.1016/j.bmc.2010.11.045
(a) Rahman, M. M.; Gray, A. I.; Khondkar, P.; Sarker, S. D. Pharm. Biol. 2008, 46, 356.
(b) Meragelman, T. L.; Tucker, K. D.; McClord, T. G.; Cardel-lina, J. H.; Shoemker, R. H. J. Nat. Prod. 2005, 68, 1790.
Hirpara, K. V.; Aggarwal, P.; Mukherjee, A. J.; Joshi, N.; Burman, A. C. Curr. Med. Chem. 2009, 9, 138.
(a) Mao, J.; Hua, Q.; Xie, G.; Guo, J.; Yao, Z.; Shi, D.; Ji, S. Adv. Synth. Catal. 2009, 351, 635.
(b) Naik, M. M.; Kamat, D. P.; Tilve, S. G.; Kamat, V. P. Tetrahedron 2014, 70, 5221.
(a) Yin, G.; Fan, L.; Ren, T.; Zheng, C.; Tao, Q.; Wu, A.; She, N. Org. Biomol. Chem. 2012, 10, 8877.
(b) Ahmed, N.; Babu, B. V. Synth. Commun. 2013, 43, 3044.
(a) Panarese, J. D.; Waters, S. P. Org. Biomol. Chem. 2013, 11, 3428.
(b) Wu, X.; Gao, Q.; Liu, S.; Wu, A. Org. Lett. 2014, 16, 2888.
(a) Wang, D. L.; Wu, D.; Zhao, W.; Wang, Y. Y.; Wu, J. Y. Chin. Chem. Lett. 2015, 26, 251.
(b) Wang, D. L.; Zhou, T.; Xing, J. J.; Qiang, J. H.; Liu, L. Heterocycles, 2016, 92, 733.
(c) Wang, D. L.; Shi, X. C.; Wang, Y. Y.; Ma, J. Chin. Chem. Lett. 2016, 27, 261.
(a) Menezes, M. J.; Manjrekar, S.; Pai, V.; Patre, R. E.; Tilve, S. G. Indian J. Chem., Sect. B 2009, 48, 1311.
(b) Gao, W.; Li, Y.; Zhang, H.; Chang, M. Q.; Imafuku, K. J. Heterocyel. Chem. 2009, 46, 1107.
Santosusso, T. M.; Swern, D. J. Org. Chem. 1975, 40, 2764.
doi: 10.1021/jo00907a013
Chen, H.; Li, J.; Chen, G. L.; Zhou, X.; Lu, X. H. Chem. Reag. 2010, 32, 80 (in Chinese).
doi: 10.3969/j.issn.0258-3283.2010.01.021
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