Chinese Journal of Organic Chemistry >
Brønsted Acid-Promoted the Synthesis of Furo[2,3-b]quinolines
Received date: 2016-12-08
Revised date: 2017-01-19
Online published: 2017-03-03
Supported by
Project supported by the National Natural Science Foundation of China (Nos.21272057,21372065),the Young Backbone Teachers Fund of Henan Province (No.2014GGJS-049),the Key Project of Henan Provincal Educational Committee (Nos.14A150019,14B150042,15A150015),the Science&Technology Innovation Talents in Universities of Henan Province (No.17HASTIT002),and the Outstanding Young Talent Cultivation Project Funding of Henan Normal University (No.14YR002).
The furoquinoline unit is present in many natural products. Here, an approach is presented for the preparing of furo[2,3-b]quinolines from readily available multi-substituted furans in the presence of Brønsted acid via an intramolecular cyclization under the heating conditions. Simple operation, good compatibility, high regioselectivity and morderate yields are the advantages of the method.
Zhang Zhiguo , Zheng Dan , Ma Na'na , Bi Jingjing . Brønsted Acid-Promoted the Synthesis of Furo[2,3-b]quinolines[J]. Chinese Journal of Organic Chemistry, 2017 , 37(7) : 1824 -1829 . DOI: 10.6023/cjoc201612032
[1] (a) Abass, M. Heterocycles 2005, 65, 901.
(b) Wang, R.; Liu, Z.-Q. Med. Chem. Res. 2013, 22, 1563.
(c) Huffman, J. W.; Browder, L. E. J. Org. Chem. 1964, 29, 2598.
[2] (a) Grougnet, R.; Magiatis, P.; Fokialakis, N.; Mitaku, S.; Skaltsounis, A. L.; Tillequin, F.; Sevenet, T.; Litaudon, M. J. Nat. Prod. 2005, 68, 1083.
(b) Ambrozin, A. R. P.; Mafezoli, J.; Vieira, P. C.; Fernandes, J. B.; da Silva, M.; Ellena, J. A.; de Albuquerque, S. J. Braz. Chem. Soc. 2005, 16, 434.
(c) Ito, C.; Itoigawa, M.; Sato, A.; Hasan, C. M.; Rashid, M. A.; Tokuda, H.; Mukainaka, T.; Nishino, H.; Furukawa, H. J. Nat. Prod. 2004, 67, 1488.
(d) Ayafor, J. F.; Okogun, J. I. J. Chem. Soc., Perkin Trans. 11982, 909.
(e) Okogun, J. I.; Ayafor, J. F. Chem. Commun. 1977, 652.
[3] (a) Mabire, D.; Coupa, S.; Adelinet, C.; Poncelet, A.; Simonnet, Y.; Venet, M.; Wouters, R.; Lesage, A. S. J.; Van Beijsterveldt, L.; Bischoff, F. J. Med. Chem. 2005, 48, 2134.
(b) Michael, J. P. Nat. Prod. Rep. 2002, 19, 742.
(c) Michael, J. P. Nat. Prod. Rep. 2004, 21, 650.
(d) Michael, J. P. Nat. Prod. Rep. 2005, 22, 627.
(e) Michael, J. P. Nat. Prod. Rep. 2003, 20, 476.
[4] Tuppy, H.; Bohm, F. Angew. Chem., Int. Ed. 1956, 68, 388.
[5] (a) Yu, L.-Z.; Hu, X.-B.; Xu, Q.; Shi, M. Chem. Commun. 2016, 52, 2701.
(b) Boyd, D. R.; Sharma, N. D.; Barr, S. A.; Carroll, J. G.; Mackerracher, D.; Malone, J. F. J. Chem. Soc., Perkin Trans. 12000, 3397.
[6] (a) Aillaud, I.; Bossharth, E.; Conreaux, D.; Desbordes, P.; Monteiro, N.; Balme, G. Org. Lett. 2006, 8, 1113.
(b) Sekar, M.; Prasad, K. J. R. J. Nat. Prod. 1998, 61, 294.
(c) Narasimhan, N. S.; Mali, R. S. Tetrahedron 1974, 30, 4153.
(d) Collins, J. F.; Gray, G. A.; Grundon, M. F.; Harrison, D. M.; Spyropoulos, C. G. J. Chem. Soc., Perkin Trans. 11973, 94.
(e) Narasimhan, N. S.; Paradkar, M. V.; Alurkar, R. H. Tetrahedron 1971, 27, 1351.
(f) Cooke, R. G.; Haynes, H. F. Aust. J. Chem. 1958, 11, 225.
(g) Grundon, M. F.; McCorkindale, N. J. J. Chem. Soc. 1957, 2177.
(h) 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.
[7] (a) Nagarajan, R.; Magesh, C. J.; Perumal, P. T. Synth. Stuttg. 2004, 69.
(b) Yadav, J. S.; Reddy, B. V. S.; Madhuri, C. R.; Sabitha, G. Synth. Stuttg. 2001, 1065.
(c) Yadav, J. S.; Reddy, B. V. S.; Gayathri, K. U.; Prasad, A. R. Synth. Stuttg. 2002, 2537.
[8] Li, X.; Wang, C; Zheng, L. Chin. J. Org. Chem. 2006, 26, 1144(in Chinese). (李雄武, 汪朝阳, 郑绿茵, 有机化学, 2006, 26, 1144.)
[9] (a) Zhang, Z.; Zhang, Q.; Sun, S.; Xiong, T.; Liu, Q. Angew. Chem., Int. Ed. 2007, 46, 1726.
(b) Ru, T. Light Ind. Sci. Technol. 2013, 5, 58(in Chinese). (茹婷婷, 轻工科技, 2013, 5, 58.)
(c) Du, W.; Curran, D. P. Org. Lett. 2003, 5, 1765.
[10] Zhang, Q.; Zhang, Z.; Yan, Z.; Liu, Q.; Wang, T. Org. Lett. 2007, 9, 3651.
[11] Zhang, Z. G. Ph.D. Dissertation, Northeast Normal University, Changchun, 2010(in Chinese). (张志国, 博士论文, 东北师范大学, 长春, 2010.)
[12] Sai, K. K. S.; Gilbert, T. M.; Klumpp, D. A. J. Org. Chem. 2007, 72, 9761.
[13] Heaney, H. In Comprehensive Organic Synthesis, Vol. 2, Eds.:Trost, B. M.; Fleming, I., Pergamon, Oxford, 1991, pp. 733~752.
[14] (a) Zhang, Z.; Zhang, Q.; Yan, Z.; Liu, Q. J. Org. Chem. 2007, 72, 9808.
(b) Xiong, T.; Zhang, Q.; Zhang, Z.; Liu, Q. J. Org. Chem. 2007, 72, 8005.
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