碱促进的新颖苯并呋喃类化合物的合成
收稿日期: 2012-05-22
修回日期: 2012-06-03
网络出版日期: 2012-06-06
基金资助
国家自然科学基金(Nos. 21072031, 20802009)、教育部博士点(新教师)基金(No. 200802461011)和上海市自然科学基金(No. 10ZR1404100)资助项目.
A Novel Strategy for the Synthesis of Benzofuran Derivatives
Received date: 2012-05-22
Revised date: 2012-06-03
Online published: 2012-06-06
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21072031, 20802009), the Ph.D. Programs Foundation of Chinese Ministry of Education (No. 200802461011) and the Shanghai Natural Science Foundation (No. 10ZR1404100).
赵云辉 , 刘文杰 , 孙兴文 , 林国强 . 碱促进的新颖苯并呋喃类化合物的合成[J]. 有机化学, 2012 , 32(10) : 1919 -1924 . DOI: 10.6023/cjoc201205028
A novel method for the synthesis of benzofuran analogues via condensation of 2-hydroxybenzaldehyde or 2-hydroxyphenyl ketone with methyl 4-bromocrotonate was reported. Moderate to good yield was obtained with cesium carbonate as base in DMF at 70 ℃. The new-generated double bond was (E)-configuration determined by X-ray diffraction. All benzofuran derivatives were determined by 1H NMR, 13C NMR and HRMS techniques.
[1] (a) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
(b) Donnelly, D. M. X.; Meegnan, M. In Comprehensive Heterocyclic Chemistry, Vol. 4, Ed.: Katrizky, A. R., Pergamon Press, New York, 1984, p. 657.
(c) Cagninant, P.; Cagninant, D. Adv. Heterocycl. Chem. 1975, 18, 337.
[2] (a) Erber, S.; Ringshandl, R.; von Angerer, E. Anti-Cancer Drug Des. 1991, 6, 417.
(b) Yoo, S.; Kim, S.-K.; Lee, S.-H.; Kim, N.-J.; Lee, D.-W. Bioorg. Med. Chem. 2000, 8, 2311.
(c) Gangjee, A.; Devraj, R.; Mcguire, J. J.; Kisliuk, R. L. J. Med. Chem. 1995, 38, 3798.
(d) Malamas, M. S.; Sredy, J.; Moxham, C.; Katz, A.; Xu, W.; McDevitt, R.; Adebayo, F. O.; Sawick, D. R.; Seestauer, L.; Sullivan, D.; Taylor, J. R. J. Med. Chem. 2000, 43,1293.
(e) Ebiike, H.; Masubuchi, M.; Liu, P.; Kawasaki, K.; Morikami, K.; Sogabe, S.; Hayase, M.; Fujii, T.; Sakata, K.; Shindoh, H.; Shiratori, Y.; Aoki, Y.; Ohtsuka, T.; Shimma, N. Bioorg. Med. Chem. Lett. 2002, 12, 607.
(f) Kawasaki, K.; Masabuchi, M.; Morikami, K.; Sogabe, S.; Aoyama, T.; Ebiike, H.; Niizuma, S.; Hayase, M.; Fujii, T.; Sakata, K.; Shindoh, H.; Shiratori, Y.; Aoki, Y.; Ohtsuka, T.; Shimma, N. Bioorg. Med. Chem. Lett. 2003, 13, 87.
(g) Masabuchi, M.; Kawasaki, K.; Ebiike, H.; Ikeda, Y.; Tsujii, S.; Sogabe, S.; Fujii, T.; Sakata, K.; Shiratori, Y.; Aoki, Y.; Ohtsuka, T.; Shimma, N. Bioorg. Med. Chem. Lett. 2001, 11, 1833.
(h) Masubuchi, M.; Ebiike, H.; Kawasaki, K.; Sogabe, S.; Morikami, K.; Shiratori, Y.; Tsujii, S.; Fujii, T.; Sakata, K.; Hayase, M.; Shindoh, H.; Aoki, Y.; Ohtsuka, T.; Shimma, N. Bioorg. Med. Chem. 2003, 11, 4463.
[3] (a) Cacchi, S.; Fabrizi, G.; Goggiomani, A. Heterocycles 2002, 56, 613.
(b) Cacchi, S.; Fabrizi, G.; Goggiamani, A. Curr. Org. Chem. 2006, 10, 1423.
(c) Hou, X.-L.; Yang, Z.; Yeung, K.-S.; Wong, H. N. C. Prog. Heterocycl. Chem. 2007, 18, 187.
(d) Byun, J. H.; Kim, H. Y.; Kim, Y. S.; Mook-Jung, I.; Kim, D. J.; Lee, W. K.; Yoo, K. H. Bioorg. Med. Chem. Lett. 2008, 18, 5591.
(e) Patil, S. A.; Patil, R.; Miller, D. D. Curr. Med. Chem. 2009, 16, 2531.
(f) De Luca, L.; Nieddu, G.; Porcheddu, A.; Giacomelli, G. Curr. Med. Chem. 2009, 16, 1.
(g) Suh, J.; Yi, K. Y.; Lee, Y.-S.; Kim, E.; Yum, E. K.; Yoo, S.-E. Bioorg. Med. Chem. Lett. 2010, 20, 6362.
[4] Chen, Y.; Chen, S.; Lu, X.; Cheng, H.; Ou, Y.; Cheng, H.; Zhou, G.-C. Bioorg. Med. Chem. Lett. 2009, 19, 1851.
[5] Geary, L. M.; Hultin, P. G. Eur. J. Org. Chem. 2010, 5563.
[6] (a) Tsai, T.-W.; Wang, E.-C.; Huang, K.-S.; Li, S.-R.; Wang, Y.-F.; Lin, Y.-L.; Chen, Y.-H. Heterocycles 2004, 63, 1771.
(b) van Otterlo, W. A. L.; Morgans, G. L.; Madeley, L. G.; Kuzvidza, S.; Moleele, S. S.; Thornton, N.; de Koning, C. B. Tetrahedron 2005, 61, 7746.
[7] (a) De Luca, L.; Giacomelli, G.; Nieddu, G. J. Org. Chem. 2007, 72, 3955.
(b) De Luca, L. Giacomelli, G. Nieddu, G. J. Comb. Chem. 2008, 10, 517.
[8] (a) Willis, M. C.; Taylor, D.; Gillmore, A. T. Org. Lett. 2004, 6, 4755.
(b) Willis, M. C.; Taylor, D.; Gillmore, A. T. Tetrahedron 2006, 62, 11513.
(c) Anderson, K. W.; Ikawa, T.; Tundel, R. E.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 10694.
(d) Ackermann, L.; Kaspar, L. T. J. Org. Chem. 2007, 72, 6149.
(e) Carril, M.; SanMartin, R.; Tellitu, I.; Dominguez, E. Org. Lett. 2006, 8, 1467.
(f) Lu, B.; Wang, B.; Zhang, Y.; Ma, D. J. Org. Chem. 2007, 72, 5337.
[9] Farago, J.; Kotschy, A. Synthesis 2009, 85.
[10] (a) Guthrie, E. J.; Macritchie, J.; Hartley, R. C. Tetrahedron Lett. 2000, 41, 4987.
(b) Nicolaou, K. C.; Snyder, S. A.; Bigot, A.; Pfefferkorn, J. A. Angew. Chem., Int. Ed. 2000, 39, 1093.
(c) Chittimalla, S. K.; Chang, T.-C.; Liu, T.-C.; Hsieh, H.-P.; Liao, C.-C. Tetrahedron 2008, 64, 2586.
(d) Sales, Z. S.; Mani, N. S. J. Org. Chem. 2009, 74, 891.
[11] (a) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285.
(b) Fuerstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024.
(c) Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 10292.
(d) Nakamura, I.; Mizushima, Y.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 15022.
(e) Grigg, R.; Sridharan, V.; Sykes, D. A. Tetrahedron 2008, 64, 8952.
(f) Isono, N.; Lautens, M. Org. Lett. 2009, 11, 1329.
[12] Guo, H.-F.; Shao, H.-Y.; Yang, Z.-Y.; Xue, S.-T.; Li, X.; Liu, Z.-Y.; He, X.-B.; Jiang, J.-D.; Zhang, Y.-Q.; Si, S.-Y.; Li, Z.-R. J. Med. Chem. 2010, 53, 1819.
[13] Matsunaga, N.; Kaku, T.; Itoh, F.; Tanaka, T.; Hara, T.; Miki, H.; Iwasaki, M.; Aono, T.; Yamaoka, M.; Kusaka, M.; Tasaka, A. Bioorg. Med. Chem. 2004, 12, 2251.
[14] (a) Han, X.; Ye, L.-W.; Sun, X.-L.; Tang, Y. J. Org. Chem. 2009, 74, 3394.
(b) Li, N.; Song, J.; Tu, X.-F.; Liu, B.; Chen, X.-H.; Gong, L.-Z. Org. Biomol. Chem. 2010, 8, 2016.
/
〈 |
|
〉 |