橙酮衍生氮杂二烯的化学反应进展

doi:10.6023/cjoc202004034

有机化学 ›› 2020, Vol. 40 ›› Issue (9): 2714-2724.DOI: 10.6023/cjoc202004034 上一篇下一篇

综述与进展

橙酮衍生氮杂二烯的化学反应进展

余述燕^a, 高丽宏^a, 兰宏兵^a, 钱恒玉^a, 尹志刚^a, 商永嘉^b

a 郑州轻工业大学材料与化学工程学院郑州 450002;
b 安徽师范大学功能分子固体教育部重点实验室安徽芜湖 240001

收稿日期:2020-04-23 修回日期:2020-05-16 发布日期:2020-06-01
通讯作者: 余述燕, 商永嘉 E-mail:yushuyan_zzuli@163.com;shyj@mail.ahnu.edu.cn
基金资助:
国家自然科学基金（No.21602207）和河南省高等学校重点研究（No.17A150022）资助项目.

Recent Progress in the Reactions of Aurone-Derived Azadienes

Yu Shuyan^a, Gao Lihong^a, Lan Hongbing^a, Qian Hengyu^a, Yin Zhigang^a, Shang Yongjia^b

a Material and Chemical Engineering College, Zhengzhou University of Light Industry, Zhengzhou 450002;
b Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000

Received:2020-04-23 Revised:2020-05-16 Published:2020-06-01
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21602207) and the Foundation of Henan Educational Committee (No. 17A150022).

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摘要/Abstract

苯并呋喃衍生物具有重要的生理和药理活性，开发高效构建具有该核心骨架化合物的合成方法具有重要的研究价值和广泛的应用前景.受分子本身芳构化驱动力的影响，橙酮衍生氮杂二烯已经成为有机合成领域一类高反应活性的合成子，大量基于1，4-共轭加成和串联环化历程的反应被陆续地报道出来，在合成具有苯并呋喃结构基元的杂环化合物方面展现出极大的应用价值.综述了近年来橙酮衍生氮杂二烯参与的化学反应进展，重点阐述了反应所采用的催化体系，并对部分反应的机理进行了讨论.

关键词: 苯并呋喃衍生物, 橙酮衍生氮杂二烯, 1,4-共轭加成, 环化反应

Owing to the important physiological and pharmacological activities of benzofuran compounds, the exploration for efficient synthesis methods is of great value and wide application. Aurone-derived azadienes have been identified to be effective reactants in the field of organic synthesis owing to the driving force of aromatization. A large number of reactions based on 1,4-conjugate addition and tandem cyclization have been reported, which exhibited great advantages in the construction of heterocycles with benzofuran skeletons. In this paper, the recent progress in the chemical transformations of aurone-derived azadienens is reviewed, with emphasis on the employed catalytic system and the plausible mechanism of some reactions.

Key words: benzofuran derivatives, aurone-derived azadienes, 1,4-conjugate addition, cyclization reactions

引用此文

余述燕, 高丽宏, 兰宏兵, 钱恒玉, 尹志刚, 商永嘉. 橙酮衍生氮杂二烯的化学反应进展[J]. 有机化学, 2020, 40(9): 2714-2724.

Yu Shuyan, Gao Lihong, Lan Hongbing, Qian Hengyu, Yin Zhigang, Shang Yongjia. Recent Progress in the Reactions of Aurone-Derived Azadienes[J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2714-2724.

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参考文献

[1] Galal, S. A.; El-All, A. S. A.; Abdallah, M. M.; El-Diwani, H. I. Bioorg. Med. Chem. Lett. 2009, 19, 2420.
(b) Shamsuzzaman, H. K. Eur. J. Med. Chem. 2015, 97, 483.
(c) Radadiya, A.; Shah, A. Eur. J. Med. Chem. 2015, 97, 356.
(d) Hiremathad, A.; Patil, M. R.; Chethana, K. R.; Chand, K.; Santos, M. A.; Keri, R. S. RSC Adv. 2015, 5, 96809.
[2] (a) Pang, J. Y.; Xu, Z. L. Chin. J. Org. Chem. 2005, 25, 25(in Chinese). (庞冀燕, 许遵乐, 有机化学, 2005, 25, 25.)
(b) Qi, J. P. Guangdong Chem. Indus. 2010, 6, 26(in Chinese). (亓金萍, 广东化工, 2010, 6, 26.)
(c) Yan, R. L. M.S. Thesis, Lanzhou University, Lanzhou, 2006 (in Chinese). (严汝龙, 硕士论文, 兰州大学, 兰州, 2006.)
[3] Gu, Z.; Zhou, J.; Jiang, G. F.; Zhou, Y. G. Org. Chem. Front. 2018, 5, 1148.
[4] Logusch, E. W.; Walker, D. M.; McDonaldand, J. F.; Franz, J. E. Biochemistry 1990, 29, 366.
[5] Dunbar, K. L.; Scharf, D. H.; Litomska, A.; Hertweck, C. Chem. Rev. 2017, 117, 5521.
[6] Zhou, Y. G.; Jiang, G. F.; Xie, J. J.; Gu, Z. Asian J. Org. Chem. 2018, 7, 1561.
[7] Roethle, P. A.; Trauner, D. Nat. Prod. Rep. 2008, 25, 298.
[8] Cui, H. L.; Huang, J. R.; Lei, J.; Wang, Z. F.; Chen, S.; Wu, L.; Chen, C. Y. Org. Lett. 2010, 12, 720.
[9] Lin, W.; Lin, X.; Cheng, Y. Y.; Chang, X. Y.; Zhou, S.; Li, P. F.; Li. W. J. Org. Chem. Front. 2019, 6, 2452.
[10] Li. W. J.; Lin, W.; Zhang, C.; Xu, W.; Cheng, Y. Y.; Li, P. F. Adv. Synth. Catal. 2019, 361, 476.
[11] Nair, V.; Thomas, S.; Mathew, S. C.; Abhilash, K. G. Tetrahedron 2006, 62, 6731.
[12] Xie, H. P.; Wu, B.; Wang, X. W.; Zhou, Y. G. Chin. J. Catal. 2019, 40, 1566.
[13] (a) Terada, M. Chem. Commun. 2008, 35, 4097.
(b) Terada, M. Synthesis 2010, 1929.
(c) Zamfir, A.; Schenker, S.; Freund, M.; Tsogoeva, S. B. Org. Biomol. Chem. 2010, 8, 5262.
[14] Wang, C. J.; Yang, Q. Q.; Wang, M. X.; Shang, Y. H.; Tong, X. Y.; Deng, Y. H.; Shao, Z. H. Org. Chem. Front. 2020, 7, 609.
[15] (a) Saracoglu, N. Top. Heterocycl. Chem. 2007, 11, 145.
(b) Kong, D.; Xue, T.; Guo, B.; Cheng, J.; Liu, S.; Wei, J.; Lu, Z.; Liu, H.; Gong, G.; Lan, T.; Hu, W.; Yang, Y. J. Med. Chem. 2019, 62, 3088.
[16] Wang, C. S.; Li, T. Z.; Chen, Y. C.; Zhou, J.; Mei, G. J.; Shi, F. J. Org. Chem. 2019, 84, 3214.
[17] (a) Khan, I. A.; Kulkarni, M. V.; Gopal, M.; Shahabuddin, M. S.; Sun, C. M. Bioorg. Med. Chem. Lett. 2005, 15, 3584.
(b) Voigt, B.; Meijer, L.; Lozach, O.; Schächtele, C.; Totzke, F.; Hilgeroth, A. Bioorg. Med. Chem. Lett. 2005, 15, 823.
[18] Zeng, R.; Shan, C. Y.; Liu, M.; Jiang, K.; Ye, Y.; Liu, T. Y.; Chen, Y. C. Org. Lett. 2019, 21, 2312.
[19] Rong, Z. Q.; Wang, M.; Hao, C.; Chow, E.; Zhao, Y. Chem.-Eur. J. 2016, 22, 9483.
[20] Gu, Z.; Wu, B.; Jiang, G. F.; Zhou, Y. G. Chin. J. Chem. 2018, 36, 1130.
[21] Li, X. P.; Yan, J. Z.; Qin, J. L.; Lin, S. L.; Chen, W. W.; Zhan, R. T.; Huang, H. C. J. Org. Chem. 2019, 84, 8035.
[22] Chen, J. L.; Jia, P. H.; Huang, Y. Org. Lett. 2018, 20, 6715.
[23] Allen, A. D.; Tidwell, T. T. Chem. Rev. 2013, 113, 7287.
[24] Bernardim, B.; Hardman-Baldwin, A. M.; Burtoloso, A. C. B. RSC Adv. 2015, 5, 13311.
[25] Tan, T.; Zhang, Z. J.; Zhang, Y. C.; Song, J. Org. Lett. 2019, 21, 7897.
[26] Xie, H. P.; Sun, L.; Wu, B.; Zhou, Y. G. J. Org. Chem. 2019, 84, 15498.
[27] (a) Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry, Higher Education Press, Beijing, 2009.
(b) Tomasi, S.; Renault, J.; Martin, B.; Duhieu, S.; Cerec, V.; LeRoch, M.; Uriac, P.; Delcros, J. G. J. Med. Chem. 2010, 53, 7647.
(c) Freidinger, R. M. J. Med. Chem. 2003, 46, 5553.
(d) Pegoraro, S.; Lang, M.; Dreker, T.; Kraus, J.; Hamm, S.; Meere, C.; Feurle, J.; Tasler, S.; Prütting, S.; Kura, Z.; Visan, V.; Grissmer, S. Bioorg. Med. Chem. Lett. 2009, 19, 2299.
[28] (a) Xie, P.; Huang, Y. Org. Biomol. Chem. 2015, 13, 8578.
(b) Wang, Z.; Xu, X.; Kwon, O. Chem. Soc. Rev. 2014, 43, 2927.
(c) Zhao, Q. Y.; Lian, Z.; Wei, Y.; Shi, M. Chem. Commun. 2012, 48, 1724.
(d) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535.
[29] Chen, J. L.; Huang, Y. Org. Lett. 2017, 19, 5609.
[30] (a) Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606.
(b) Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. Nature 2014, 510, 485.
(c) Bugaut, X.; Glorius, F. Chem. Soc. Rev. 2012, 41, 3511.
(d) Grossmann, D. A.; Enders, D. Angew. Chem.. Int. Ed. 2012, 51, 314.
[31] Gao, Z. H.; Chen, K. Q.; Zhang, Y.; Kong, L. M.; Li, Y.; Ye, S. J. Org. Chem. 2018, 83, 15225.
[32] Chen, K. Q.; Gao, Z. H.; Ye, S. Org. Chem. Front. 2019, 6, 405.
[33] (a) Trost, B. M. Angew. Chem.. Int. Ed. 1986, 25, 1.
(b) Trost, B. M. Pure Appl. Chem. 1988, 60, 1615.
[34]
[33] Shintani, R.; Park, S.; Duan, W. L.; Hayashi, T. Angew. Chem.. Int. Ed. 2007, 46, 5901.
[35] Trost, B. M.; Zuo, Z. J. Angew. Chem.. Int. Ed. 2020, 59, 1243.
[36] (a) Hussain, A.; Yousuf, S. K.; Mukherjee, D. RSC Adv. 2014, 4, 43241.
(b) Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 251.
(c) Mallinson, J.; Collins, I. Future Med. Chem. 2012, 4, 1409.
(d) Brown, H. C.; Fletcher, R. S.; Johannesen, R. B. J. Am. Chem. Soc. 1951, 73, 212.
(e) Prelog, V. Pure Appl. Chem. 1963, 6, 545.
[37] Ni, H. Z.; Tang, X. D.; Zheng, W. R.; Yao, W. J.; Ullah, N.; Lu, Y. X. Angew. Chem.. Int. Ed. 2017, 56, 14222.
[38] (a) Evans, A. E.; Farber, S.; Brunet, S.; Mariano, P. J. Cancer 1963, 16, 1302.
(b) Armstrong, J. G.; Dyke, R. W.; Fouts, P. J. Science 1964, 143, 703.
(c) Shimokawa, T.; Kinjo, J.; Yamahara, J.; Yamasaki, M.; Nohara, T. Chem. Pharm. Bull. 1985, 33, 3545.
[39] Yang, L. C.; Rong, Z. Q.; Wang, Y. N.; Tan, Z. Y.; Wang, M.; Zhao, Y. Angew. Chem.. Int. Ed. 2017, 56, 2927.
[40] Rong, Z. Q.; Yang, L. C.; Liu, S.; Yu, Z. Y.; Wang, Y. N.; Tan, Z. Y.; Huang, R. Z.; Lan, Y.; Zhao, Y. J. Am. Chem. Soc. 2017, 139, 15304.
[41] Wang, Y. N.; Yang, L. C.; Rong, Z. Q.; Liu, T. L.; Liu, R. Y.; Zhao, Y. Angew. Chem.. Int. Ed. 2018, 57, 1596.
[42] (a) Lee, S. H.; Seo, H. J.; Lee, S. H.; Jung, M. E.; Park, J. H.; Park, H. J.; Yoo, J.; Yun, H.; Na, J.; Kang, S. Y.; Song, K. S.; Kim, M.; Chang, C. H.; Kim, J.; Lee, J. J. Med. Chem. 2008, 51, 7216.
(b) Bilich, A.; Winther, M. D. Chem. Abstr. 2008, 149, 556638.
(c) Barnes-Seeman, D.; Jain, M.; Bell, L.; Ferreira, S.; Cohen, S.; Chen, X. H.; Amin, J.; Snodgrass, B.; Hatsis, P. ACS Med. Chem. Lett. 2013, 4, 514.
(d) Bezençon, O.; Heidmann, B.; Siegrist, R.; Stamm, S.; Richard, S.; Pozzi, D.; Corminboeuf, O.; Roch, C.; Kessler, M.; Ertel, E. A.; Reymond, I.; Pfeifer, T.; de Kanter, R.; Toeroek-Schafroth, M.; Moccia, L. G.; Mawet, J.; Moon, R.; Rey, M.; Capeleto, B.; Fournier, E. J. Med. Chem. 2017, 60, 9769.
[43] Bos, M.; Poisson, T.; Pannecoucke, X.; Charette, A. B.; Jubault, P. Eur. J. Chem. 2017, 23, 495.
[44] Chen, T.; Zhang, Y.; Fu, Z. Q.; Huang, W. Asian J. Org. Chem. 2019, 8, 2175.
[45] Marques, A. S.; Duhail, T.; Marrot, J.; Chataigner, I.; Coeffard,V.; Vincent, G.; Moreau, X. Angew. Chem.. Int. Ed. 2019, 58, 9969.
[46] Qi, J. F.; Tang, H. B.; Chen, C. W.; Cui, S. L.; Xu, G. Org. Chem. Front. 2019, 6, 2760.

橙酮衍生氮杂二烯的化学反应进展

Recent Progress in the Reactions of Aurone-Derived Azadienes

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