Chinese Journal of Organic Chemistry >
A Facile and New Synthetic Method of Polysubstituted Furans
Received date: 2015-03-16
Revised date: 2015-03-30
Online published: 2015-04-10
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21272119, 21121002), and the Natural Science Foundation of Hubei Province (No. 2007ABA375).
With the treatment of tributylphosphine and base, alkynoates, aromatic aldehydes and acyl chlorides readily undergo a four-component cascade annulation reaction, giving tri-or tetra-substituted furans in moderate yields. The reaction presumably proceeds through an intramolecular Wittig reaction step of the in situ generated phosphorus ylide intermediate. The annulation reaction features mild reaction conditions and broad substrate scope, and accordingly constitutes a facile and new synthetic method of polysubstituted furans.
Key words: furans; synthesis; phosphines; multicomponent reactions; Wittig reaction
Zou Wen , He Zheng-Rong , He Zhengjie . A Facile and New Synthetic Method of Polysubstituted Furans[J]. Chinese Journal of Organic Chemistry, 2015 , 35(8) : 1739 -1745 . DOI: 10.6023/cjoc201503022
[1] (a) Dean, F. M. Naturally Occurring Oxygen Ring Compounds, Butterworths, London, 1963, pp. 1~28. (b) Donnelly, D. M. X.; Meegan, M. J. In Comprehensive Heterocyclic Chemistry, Vol. 4, Ed.: Katrizky, A. R., Pergamon Press, New York, 1984, pp. 657~712. (c) Landquist, J. K. In Comprehensive Heterocyclic Chemistry, Vol. 1, Ed.: Katrizky, A. R., Pergamon Press, New York, 1984, pp. 144~184. (d) Cacchi, S. J. Organomet. Chem. 1999, 576, 42.
[2] (a) Lipshutz, B. H. Chem. Rev. 1986, 86, 795. (b) Wong, H. N. C.; Yang, Y. Tetrahedron 1994, 50, 9583. (c) Lee, H.-K.; Chan, K.-F.; Hui, C.-W.; Yim, H.-K.; Wu, X.-W.; Wong, H. N. C. Pure Appl. Chem. 2005, 77, 139.
[3] (a) Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y. T.; Wong, H. N. C. Tetrahedron 1998, 54, 1955. (b) Keay, B. A. Chem. Soc. Rev. 1999, 28, 209. (c) Ma, S. Acc. Chem. Res. 2003, 36, 701. (d) Brown, R. C. D. Angew. Chem., Int. Ed. 2005, 44, 850. (e) Kirsch, S. F. Org. Biomol. Chem. 2006, 4, 2076.
[4] For representative examples, see: (a) Calter, M. A.; Zhu, C.; Lachicotte, R. J. Org. Lett. 2002, 4, 209. (b) Minetto, G.; Raveglia, L. F.; Sega, A.; Taddei, M. J. Org. Chem. 2005, 70, 5277, and references cited therein. (c) Mross, G.; Holtz, E.; Langer, P. J. Org. Chem. 2006, 71, 8045.
[5] For selected examples, see: (a) Barluenga, J.; Riesgo, L.; Vicente, R.; Lopez, L. A.; Tomas, M. J. Am. Chem. Soc. 2008, 130, 13528. (b) Aurrecoechea, J. M.; Durana, A.; Perez, E. J. Org. Chem. 2008, 73, 3650. (c) Li, Y.; Yu, Z. J. Org. Chem. 2009, 74, 8904. (d) Cao, H.; Jiang, H.; Yao, W.; Liu, X. Org. Lett. 2009, 11, 1931. (e) Cao, H.; Jiang, H.; Yuan, G.; Chen, Z.; Qi, C.; Huang, H. Chem. Eur. J. 2010, 16, 10553. (f) Cao, H.; Jiang, H.; Mai, R.; Zhu, S.; Qi. C. Adv. Synth. Catal. 2010, 352, 143. (g) Wang, Y.; Xu, L.; Ma, D. Chem. Asian J. 2010, 5, 74. (h) Zhang, X.; Lu, Z.; Fu, C.; Ma. S. J. Org. Chem. 2010, 75, 2589. (i) Liu, W.; Jiang, H.; Zhang, M.; Qi, C. J. Org. Chem. 2010, 75, 966. (j) Yang, J.; Wang, C.; Xie, X.; Li, H.; Li, E.; Li, Y. Org. Biomol. Chem. 2011, 9, 1342. (k) Chen, Z.; Huang, G.; Jiang, H.; Huang, H.; Pan, X. J. Org. Chem. 2011, 76, 1134.
[6] (a) Jung, C.-K.; Wang, J.-C.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 4118. (b) Kao, T.-T.; Syu, S.-E.; Jhang, Y.-W.; Lin, W. Org. Lett. 2010, 12, 3066. (c) Chen, K.-W.; Syu, S.-E.; Jang, Y.-J.; Lin, W. Org. Biomol. Chem. 2011, 9, 2098. (d) Syu, S.-E.; Lee, Y.-T.; Jang, Y.-J.; Lin, W. Org. Lett. 2011, 13, 2970. (e) Wang, Y.; Luo, Y.-C.; Hu, X.-Q.; Xu, P.-F. Org. Lett. 2011, 13, 5346. (f) Hu, J.; Wei, Y.; Tong, X. Org. Lett. 2011, 13, 3068. (g) Wang, J.; Zhou, R.; He, Z.-R.; He, Z. Eur. J. Org. Chem. 2012, 6033. (h) Fan, Y.-S.; Das, U.; Hsiao, M.-Y.; Liu, M.-H.; Lin, W. J. Org. Chem. 2014, 79, 11567. (i) Das, U.; Tsai, Y.-L.; Lin, W. Org. Biomol. Chem. 2014, 12, 4044.
[7] For recent related reports from our group, see: (a) Tian, J.; Zhou, R.; Song, H.; He, Z. J. Org. Chem. 2011, 76, 2374. (b) Tian, J.; Sun, H.; Zhou, R.; He, Z. Chin. J. Chem. 2013, 31, 1348. (c) Zhou, R.; Wang, J.; Yu, J.; He, Z. J. Org. Chem. 2013, 78, 10596. (d) Zhou, R.; Duan, C.; Yang, C.; He, Z. Chem. Asian J. 2014, 9, 1183. (e) Yang, M.; Wang, T.; Cao, S.; He, Z. Chem. Commun. 2014, 50, 13506. (f) Xu, S.; He, Z. Chin. J. Org. Chem. 2014, 34, 2438 (in Chinese). (徐四龙, 贺峥杰, 有机化学, 2014, 34, 2438.) (g) Zhou, R.; Liu, R.; Li, R.; He, Z. Chin. J. Org. Chem. 2014, 34, 2385 (in Chinese). (周荣, 刘蓉芳, 李瑞丰, 贺峥杰, 有机化学, 2014, 34, 2385.)
[8] Zhu, X.-F.; Henry, C. E.; Kwon, O. J. Am. Chem. Soc. 2007, 129, 6722.
[9] This compound was reported without its characterization data in the following reference: Pohmakotr, M.; Issaree, A.; Sampaongoen, L.; Tuchinda, P.; Reutrakul, V. Tetrahedron Lett. 2003, 44, 7937.
[10] Hsu, D. T.; Lin, C. H. J. Org. Chem. 2009, 74, 9180.
[11] The synthesis of this compound is reported in reference [6c], but there are some errors in its NMR data. A reported compound without characterization data, Koenig, B. Sci. Synth. 2002, 9, 183.
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