Reviews

Recent Progress in Synthesis of Polysubstituted Furans

  • Zhang Wensheng ,
  • Xu Wenjing ,
  • Zhang Fei ,
  • Li Yan
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  • a Jiaozuo Teachers College, Jiaozuo 454100;
    b Jiaozuo Vocational and Technological School, Jiaozuo 454100

Received date: 2018-11-18

  Revised date: 2018-12-25

  Online published: 2019-01-18

Supported by

Project supported by the Foundation and Frontier Research Program (the Natural Science Foundation) of Henan Province (No. 162300410270).

Abstract

Furan, an important class of oxygen-containing five-membered heterocyclic compounds, is not only the fundamental structure of many natural products, drugs and biologically active molecules, but also an valuable intermediate in organic synthesis. Synthesis of polysubstituted furans has been one of the focus of organic chemists. In this paper, recent progress in the synthesis of polysubstituted furans since 2013, including disubstituted, trisubstituted, tetrasubstituted furans and benzofurans is reviewed.

Key words: furan; synthesis; cyclization

Cite this article

Zhang Wensheng , Xu Wenjing , Zhang Fei , Li Yan . Recent Progress in Synthesis of Polysubstituted Furans[J]. Chinese Journal of Organic Chemistry, 2019 , 39(5) : 1277 -1283 . DOI: 10.6023/cjoc201811023

References

[1] (a) Hou, X. L.; Yang, Z.; Wong, H. N. C. Prog. Heterocycl. Chem. 2003, 15, 167.
(b) Keay, B. A.; Dibble, P. W. In Comprehensive Heterocyclic Chemistry Ⅱ, Vol. 2, Eds.:Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Elsevier, Oxford, 1997, p. 395.
(c) Suhre, M. H.; Reif, M.; Kirsch, S. F. Org. Lett. 2005, 7, 3925.
(d) Rao, A. U.; Xiao, D.; Huang, X.; Zhou, W.; Fossetta, J.; Lundell, D.; Tian, F.; Trivedi, P.; Aslanian, R.; Palani, A. Bioorg. Med. Chem. Lett. 2012, 22, 1068.
(e) Kumari, N.; Mishra, C. B.; Prakash, A.; Kumar, N.; Mongre, R.; Luthra, P. M. Neurosci. Lett. 2014, 558, 203.
(f) Hasegawa, F.; Niidome, K.; Migihashi, C.; Murata, M.; Negoro, T.; Matsumoto, T.; Kato, K.; Fujii, A. Bioorg. Med. Chem. Lett. 2014, 24, 4266.
[2] (a) Kalaitzakis, D.; Triantafyllakis, M.; Alexopoulou, I.; Sofiadis, M.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2014, 53, 13201.
(b) Wang, Z.-L.; Li, H.-L.; Ge, L.-S.; An, X.-L.; Zhang, Z.-G.; Luo, X.; Fossey, J. S.; Deng, W.-P. J. Org. Chem. 2014, 79, 1156.
[3] (a) Zeng, C.; Seino, H.; Ren, J.; Hatanaka, K.; Yoshie, N. Macromolecules 2013, 46, 1794.
(b) Zeng, C.; Seino, H.; Ren, J.; Hatanaka, K.; Yoshie, N. Polymer 2013, 54, 5351.
(c) Gidron, O.; Shimon, L. J. W.; Leitus, G.; Bendikov, M. Org. Lett. 2012, 14, 502.
(d) Gidron, O.; Dadvand, A.; Sheynin, Y.; Bendikov, M.; Perepichka, D. F. Chem. Commun. 2011, 47, 1976.
(e) Bunz, U. H. F. Angew. Chem., Int. Ed. 2010, 49, 5037.
(f) Gidron, O.; Diskin-Posner, Y.; Bendikov, M. J. Am. Chem. Soc. 2010, 132, 2148.
[4] Pérez, J. M.; Cano, R.; Yus, M.; Ramón, D. J. Synthesis 2013, 45, 1373.
[5] Reddy, C. R.; Krishna, G.; Reddy, M. D. Org. Biomol. Chem. 2014, 12, 1664.
[6] Fan, W.; Ma, S. M. Eur. J. Org. Chem. 2015, 3531.
[7] Yang, Y. Z.; Yao, J. Z.; Zhang, Y. H. Org. Lett. 2013, 15, 3206.
[8] Ghosh, M.; Mishra, S.; Monir, K.; Hajra, A. Org. Biomol. Chem. 2015, 13, 309.
[9] Wang, T.; Shi, S.; Hansmann, M. M.; Rettenmeier, E.; Rudolph, M.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2014, 53, 3715.
[10] Deng, J. C.; Chuang, S. C. Org. Lett. 2014, 16, 5792.
[11] Ghosh, M.; Mishra, S.; Hajra, A. J. Org. Chem. 2015, 80, 5364.
[12] Tang, S.; Liu, K.; Long, Y.; Qi, X. T.; Lan, Y.; Lei, A. W. Chem Commun. 2015, 8769.
[13] Yu, Y.; Yi, S. G.; Zhu, C. L.; Hu, W. G.; Gao, B. J.; Chen, Y.; Wu, W. Q.; Jiang, H. F. Org. Lett. 2016, 18, 400.
[14] Dey, A.; Ali, M. A.; Jana, S.; Hajra, A. J. Org. Chem. 2017, 82, 4812.
[15] Chen, R. S.; Fan, X.; Xu, Z. Z.; He, Z. J. Tetrahedron Lett. 2017, 58, 3722.
[16] Zhang, W. S.; Xu, W. J. Chem. Heterocycl. Compd. 2017, 53, 615.
[17] He, T.; Gao, P.; Qiu, Y. F.; Yan, X. B.; Liu, X. Y.; Liang, Y. M. RSC Adv. 2013, 13, 19913.
[18] Ma, Y. H.; Zhang, S.; Yang, S. P.; Song, F. J.; You, J. S. Angew. Chem., Int. Ed. 2014, 53, 7870.
[19] Nitsch, D.; Bach, T. J. Org. Chem. 2014, 79, 6372.
[20] Song, C. L.; Wang, J. W.; Xu, Z. H. Org. Biomol. Chem. 2014, 12, 5802.
[21] Yue, Y. Y.; Zhang, Y. L.; Song, W. W.; Zhang, X.; Liu, J. M.; Zhuo, K. L. Adv. Synth. Catal. 2014, 356, 2459.
[22] Reddy, C. R.; Mohammed, S. Z.; Kumaraswamy, P. Org. Biomol. Chem. 2015, 13, 8310.
[23] Mane, V.; Kumar, T.; Pradhan, S.; Katiyar, S.; Namboothiri, I. N. N. RSC Adv. 2015, 5, 69990.
[24] Zou, W.; He, Z. R.; He, Z. J. Chin. J. Org. Chem. 2015, 35, 1739(in Chinese). (邹雯, 贺峥嵘, 贺峥杰, 有机化学, 2015, 35, 1739.)
[25] Liu, J. M.; Ye, W. J.; Qing, X. S.; Wang, C. D. J. Org. Chem. 2016, 81, 7970.
[26] Pathipati, S. R.; Werf, A.; Eriksson, L.; Selander, N. Angew. Chem., Int. Ed. 2016, 55, 11863.
[27] Kuram,M. R.; Bhanuchandra, M.; Sahoo, A. K. Angew. Chem., Int. Ed. 2013, 52, 4607.
[28] Sharma, U.; Naveen, T.; Maji, A.; Manna, S.; Maiti, D. Angew. Chem., Int. Ed. 2013, 52, 12669.
[29] Yuan, H.; Bi, K. J.; Li, B.; Yue, R. C.; Ye, J.; Shen, Y. H.; Shan, L.; Jin, H. Z.; Sun, Q. Y.; Zhang, W. D. Org. Lett. 2013, 15, 4742.
[30] Markina, N. A.; Chen, Y.; Larock, R. C. Tetrahedron 2013, 69, 2701.
[31] Osyanin, V. A.; Osipov, D. V.; Demidov, M. R.; Klimochkin, Y. R. N. J. Org. Chem. 2014, 79, 1192.
[32] Tsuji, H.; Ilies, L.; Nakamura, E. Synlett 2014, 25, 2099.

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