A Facile Synthesis of Novel Pyridine-2,6-diylbis(1-benzofuran-2- ylmethanone) Derivatives under Ultrasonic Conditions

doi:10.6023/cjoc201206003

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (11): 2171-2176.DOI: 10.6023/cjoc201206003 Previous Articles Next Articles

Notes

超声波辅助下新型2,6-二-(苯并呋喃-2-甲酰基)吡啶衍生物的简便合成

高文涛, 陶希月, 林贵海, 李阳

渤海大学超精细化学品研究所锦州 121000

收稿日期:2012-06-05 修回日期:2012-07-04 发布日期:2012-07-11
通讯作者: 高文涛 E-mail:isfc@bhu.edu.cn
基金资助:
辽宁省自然科学基金(No. 2012S001)资助项目.

A Facile Synthesis of Novel Pyridine-2,6-diylbis(1-benzofuran-2- ylmethanone) Derivatives under Ultrasonic Conditions

Gao Wentao, Tao Xiyue, Lin Guihai, Li Yang

Institute of Superfine Chemicals, Bohai University, Jinzhou 121000

Received:2012-06-05 Revised:2012-07-04 Published:2012-07-11
Supported by:
Project supported by the Natural Science Foundation of Liaoning Province (No. 2012S001).

A facile synthesis of unreported pyridine-2,6-diylbis(benzofuran-2-ylmethanone) derivatives was described. The synthesis mainly relied on the ultrasound-assisted Rap-Stoermer reaction of 1,1'-(pyridine-2,6-diyl)bis(2-bromoethanone) with a variety of salicylaldehydes in MeCN at the presence of PEG-400. This procedure offered easy access to construct new prototypes containing methanone linker between the benzo(naphtho)furan ring and pyridine moiety at 2,6-position in a short reaction time and mild conditions with good yields. Compound structures were identified by means of ¹H(¹³C) NMR, IR and elemental analysis.

Key words: 1,1'-(pyridine-2,6-diyl)bis(2-bromoethanone), benzo(naphtho)furan, carbonyl group, ultrasound-assisted, Rap- Stoermer reaction

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Gao Wentao, Tao Xiyue, Lin Guihai, Li Yang. A Facile Synthesis of Novel Pyridine-2,6-diylbis(1-benzofuran-2- ylmethanone) Derivatives under Ultrasonic Conditions[J]. Chin. J. Org. Chem., 2012, 32(11): 2171-2176.

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[1] Fichera, M.; Gregoli, L.; Musumarra, G. J. Phys. Org. Chem. 2000, 13, 344.

[2] Jacquemard, U.; Dias, N.; Lansiaux, A.; Bailly, C.; Logé, C.; Robert, J. M.; Lozach, O.; Meijer, L.; Mérour, J. Y.; Routier, S. Bioorg. Med. Chem. 2008, 16, 4932.

[3] Barresi, V.; Condorelli, D. F.; Fortuna, C. G.; Musumarra, G.; Scirè, S. Bioorg. Med. Chem. 2002, 10, 2899.

[4] Jäger, M.; Eriksson, L.; Bergquist, J.; Johansson, O. J. Org. Chem. 2007, 72, 10227.

[5] Onozawa-Komatsuzaki, N.; Yanagida, M.; Funaki, T.; Kasuga, K.; Sayama, K.; Sugihara, H. Inorg. Chem. Commun. 2009, 12, 1212.

[6] Hurtado, J.; Ugarte, J.; Rojas, R.; Valderrama, M.; Carey, D. M. L.; Muñoz-Castro, A.; Arratia-Pérez, R.; Fröhlich, R. Inorg. Chim. Acta 2011, 378, 218.

[7] Li, C. J.; Guo, Q. B.; Yin, G. Q.; Jiang, X. H.; Gong, S. Chin. J. Chem. 2011, 29, 1395.

[8] Brien, K. A.; Garner, C. M.; Pinney, K. G. Tetrahedron 2006, 62, 3663.

[9] Duncan, N. C.; Garner, C. M. Tetrahedron Lett. 2011, 52, 5214.

[10] Zhang, J.; Zhang, M.; Cao, W.; Song, L.; Qian, Q.; Tan, J. Heteroat. Chem. 2009, 20, 123.

[11] Hayakawa, I.; Shioya, R.; Agatsuma, T.; Furukawa, H.; Naruto, S.; Sugano, Y. Bioorg. Med. Chem. Lett. 2004, 14, 4383.

[12] Alper-Hayta, S.; Arisoy, M.; Temiz-Arpaci, Ö.; Yildiz, I.; Aki, E.; Özkan, S.; Kaynak, F. Eur. J. Med. Chem. 2008, 43, 2568.

[13] Dawood, K. M.; Abdel-Gawad, H.; Rageb, E. A.; Ellithey, M.; Mohamed, H. A. Bioorg. Med. Chem. 2006, 14, 3672.

[14] Romagnoli, R.; Baraldi, P. G.; Carrion, M. D.; Cara, C. L.; Cruz-Lopez, O.; Tolomeo, M.; Grimaudo, S.; Cristina, A. D.; Pipitone, M. R.; Balzarini, J.; Zonta, N.; Brancale, A.; Hamel, E. Bioorg. Med. Chem. 2009, 17, 6862.

[15] Kawasaki, K.; Masubuchi, 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.

[16] Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365.

[17] Saberi, M. R.; Vinh, T. K.; Yee, S. W.; Griffiths, B. J. N.; Evans, P. J.; Simons, C. J. Med. Chem. 2006, 49, 1016.

[18] Liu, Y.; Qian, J.; Lou, S.; Xu, Z. J. Org. Chem. 2010, 75, 6300.

[19] Saku, O.; Saki, M.; Kurokawa, M.; Ikeda, K.; Takizawa, T.; Uesaka, N. Bioorg. Med. Chem. Lett. 2010, 20, 1090.

[20] Parekh, S.; Bhavsar, D.; Savant, M.; Thakrar, S.; Bavishi, A.; Parmar, M.; Vala, H.; Radadiya, A.; Pandya, N.; Serly, J.; Molnár, J.; Shah, A. Eur. J. Med. Chem. 2011, 46, 1942.

[21] Zhang, D. F.; Xie, G.. Y. C. Chem. Reag. 2008, 30, 49 (in Chinese).
(张东方, 谢光勇, 化学试剂, 2008, 30, 49.)

[22] Deady, L. W.; Stanborough, M. S. Aust. J. Chem. 1981, 34, 1295.

[23] Gao, W. T.; Zhang, C. H.; Li, Y. J. Braz. Chem. Soc. 2010, 21, 806.

[24] Gao, W. T.; Liu, J.; Jiang, Y.; Li, Y. Beilstein J. Org. Chem. 2011, 7, 210.

[25] Gao, W. T.; Zheng, M. R.; Li, Y. Beilstein J. Org. Chem. 2011, 7, 1533.

[26] Li, Y.; Yan, Y.; Gao, W. T. Heterocycles 2012, 85, 421.

[27] Gao, W. T.; Jiang, Y.; Li, Y.; Li, F.; Yan, Y. Chin. J. Chem. 2012, 30, 822.

[28] Luche, J. L. Synthetic Organic Sonochemitry, Plenum Press, New York, 1998.

[29] Mason, T. J.; Peter, D. Pratical Sonochemistry, 2nd ed., Eills Horwood, London, 2002.

[30] Wang, M. L.; Chang, K. R. Can. J. Chem. Eng. 1991, 69, 340.

[31] Tatum, J. H.; Baker, R. A.; Berry, R. E. Phytochemistry 1987, 26, 2499.

[32] Stipanovic, R. D.; Bell, A. A.; Howell, C. R. Phytochemistry 1975, 14, 1809.

[33] Goel, A.; Dixit, M. Tetrahedron Lett. 2004, 45, 8819.

[34] Piloto, A. M.; Costa, S. P. G.; Goncalves, M. S. T. Tetrahedron Lett. 2005, 46, 4757.

[35] Srivastava, V.; Negi, A. S.; Kumar, J. K.; Faridi, U.; Sisodia, B. S.; Darokar, M. P.; Luqman, S.; Khanuja, S. P. S. Bioorg. Med. Chem. Lett. 2006, 16, 91.

超声波辅助下新型2,6-二-(苯并呋喃-2-甲酰基)吡啶衍生物的简便合成

A Facile Synthesis of Novel Pyridine-2,6-diylbis(1-benzofuran-2- ylmethanone) Derivatives under Ultrasonic Conditions

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