SIOC English
有机化学
高级检索

有机化学 >

2020 , Vol. 40 >Issue 5: 1384 - 1387

DOI: https://doi.org/10.6023/cjoc201910003

研究简报

微波促进I2催化吲哚3-硒氰酸化制备3-硒氰酸吲哚衍生物

  • 吴燕 ,
  • 田仙芝 ,
  • 张海玲 ,
  • 陈睿 ,
  • 曹团武
展开
  • 长江师范学院化学化工学院 无机特种材料重庆市重点实验室 涪陵 408000

收稿日期: 2019-10-06

  修回日期: 2019-12-03

  网络出版日期: 2020-01-03

基金资助

重庆市基础前沿研究（Nos.Cstc2018jcyjAX0721，Cstc2016jcyjA0056）、长江师范学院青年人才成长计划（No.2018QNRC11）、重庆市教育委员会（No.KJQN201801404）资助项目.

收起

Microwave-Assisted Iodine-Catalyzed 3-Selenocyanation of Indole for the Synthesis of 3-Selenocyanateindole Derivatives

  • Wu Yan ,
  • Tian Xianzhi ,
  • Zhang Hailing ,
  • Chen Rui ,
  • Cao Tuanwu
Expand
  • Chongqing Key Laboratory of Inorganic Special Functional Materials, College of Chemistry and Chemical Engineering, Yangtze Normal University, Fuling 408000

Received date: 2019-10-06

  Revised date: 2019-12-03

  Online published: 2020-01-03

Supported by

Project supported by the Basic and Frontier Research Project of Chongqing City (Nos. Cstc2018jcyjAX0721, Cstc2016jcyjA0056), the Youth Talent Growth Plan Project of Yangtze Normal University (No. 2018QNRC11), and the Education Commission of Chongqing City (No. KJQN201801404).

Fold

摘要

3-硒氰酸吲哚衍生物由于良好的生物活性，在药物研究方面具有潜在的应用价值.目前，关于3-硒氰酸吲哚的制备方法存在一定的不足，如反应条件苛刻、产率较低、底物适用性较差等.采用微波促进I2催化吲哚与硒氰酸钾的反应，制备了一系列3-硒氰酸吲哚衍生物.与已有方法相比，本方法具有反应速率快、产率高、原子经济性好等优点，为3-硒氰酸吲哚衍生物的制备提供高效的路径.

关键词： 微波辅助反应; 碘催化硒氰酸化; 3-硒氰酸吲哚; 吲哚衍生物; 硒氰酸钾

本文引用格式

吴燕 , 田仙芝 , 张海玲 , 陈睿 , 曹团武 . 微波促进I2催化吲哚3-硒氰酸化制备3-硒氰酸吲哚衍生物[J]. 有机化学, 2020 , 40(5) : 1384 -1387 . DOI: 10.6023/cjoc201910003

Abstract

3-Selenocyanateindole derivatives have potential application in drug research due to their good biological activity. Until now, many methods for the synthesis of 3-selenocyanateindoles have been reported. However, drawbacks still exist, such as harsh reaction conditions, low yields and poor functional groups tolerance. A series of 3-selenocyanateindoles have been synthesized via the microwave-assisted 3-selenocyanation of indole derivatives by using 25 mol% iodine as catalyst, affording the corresponding products in good yields. Compared with the previous methods, this protocol has the advantages of rapid reaction, high yields and good atomic economy, providing an efficient route to 3-selenocyanateindole derivatives.

Key words： microwave-assisted reaction; iodine-catalyzed selenocyanation; 3-selenocyanate iodines; iodine derivatives; potassium selenocyanate

参考文献

[1] Li, Y.; Chen, S.; Su, L.; Li, J. Chin. J. Org. Chem. 2013, 33, 1999(in Chinese). (李媛媛, 陈四海, 苏柳, 李建华, 有机化学, 2013, 33, 1999.)
[2] Turner, D. C.; Stadtman, T. C. Arch. Biochem. Biophys. 1973, 25, 187.
[3] Zhou, F.; Yang, W.; Wang, M.; Miao, Y.; Cui, Z.; Li, Z.; Liang, D. Food Chem. 2018, 265, 182.
[4] Wang, X.; Li, Z.; Zhang, W.; Wang, X.; Chen, J.; Li, N.; Qiu, R.; Xu. X. Chin. J. Org. Chem. 2013, 33, 558(in Chinese). (王小勇, 李治章, 张卫军, 王勰, 陈锦杨, 李宁波, 邱仁华, 许新华, 有机化学, 2013, 33, 558.)
[5] Reich, H. J.; Renga, J. M.; Reich, I. L. J. Am. Chem. Soc. 1975, 97, 19.
[6] Reich, H. J.; Reich, I. L.; Renga, J. M. J. Am. Chem. Soc. 1973, 95, 17.
[7] Liu, W.; Yin, X.; Zang, Z.; Yu, X.; Tao, L.; Li, Y.; Xu, X. Chin. J. Org. Chem. 2009, 29, 2021(in Chinese). (刘文奇, 尹显洪, 臧中林, 余晓芬, 陶李明, 李言杰, 许新华, 有机化学, 2009, 29, 2021.)
[8] Reich, H. J. Chem. Rev. 2013, 113, 7130.
[9] Lu, L-H.; Wang, Z.; Xia, W.; Cheng, P.; Zhang, B.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2019, 30, 1237.
[10] Kolonko, K. J.; Guzei, I. A.; Reich, H. J. J. Org. Chem. 2010, 75, 6163.
[11] Wang, F.; Xu, L.; Sun, C.; Xu, Q.; Huang, J. Yu, L. Chin. J. Org. Chem. 2017, 37, 2115(in Chinese). (王芳, 徐林, 孙诚, 徐清, 黄杰军, 俞磊, 有机化学, 2017, 37, 2115.)
[12] Mukherjee, A. J.; Zade, S. S.; Singh, H. B.; Sunoj, R. B. Chem. Rev. 2010, 110, 4357.
[13] Quatrin, P. M.; Dalla, L.; Daiane, F.; Bazana, L. C. G.; de Oliveira, L. F. S.; Lettieri, T. M.; Silva, E. E.; Lopes, W.; Canto, R. F. S.; Silveira, G. P.; Fuentefria, A. M. New J. Chem. 2019, 43, 926.
[14] Guan, Q.; Han, C.; Zuo, D.; Zhai, M.; Li, Z.; Zhang, Q.; Zhai, Y.; Jiang, X.; Bao, K.; Wu, Y.; Zhang, W. Eur. J. Med. Chem. 2014, 87, 306.
[15] Muniraj, N.; Dhineshkumar, J.; Prabhu, K. R. ChemistrySelect 2016, 1, 1033.
[16] Wang, X.; Mu, S.; Sun, T.; Sun, K. Chin. J. Org. Chem. 2019, 39, 2808(in Chinese). (王薪, 穆石强, 孙婷, 孙凯, 有机化学, 2019, 39, 2808.)
[17] Abonia, R.; Gutierrez, L. F.; Zwarycz, A. T.; Smits, S. C.; Laali, K. K. Heteroat. Chem. 2019, 1459681.
[18] Feng, C.; Peng, Y.; Ding, G.; Li, X.; Cui, C.; Yan, Y. Chem. Commun. 2018, 54, 13367.
[19] Nair, V.; Augustine, A.; George, T. G. Eur. J. Org. Chem. 2002, 14, 2363.
[20] Kachanov, A. V.; Slabko, O. Y.; Baranova, O. V.; Shilova, E. V.; Kaminskii, V. A. Tetrahedron Lett. 2004, 45, 4461.
[21] Zhang, X.; Wang, C.; Jiang, H.; Sun, L. RSC Adv. 2018, 8, 22042.
[22] Liang, L.; Li, J.; Zhang, Q.; Ma, H. Chin. J. Org. Chem. 2019, 39, 1323(in Chinese). (梁玲, 牟佳玲, 陈悦, 王梦莎, 洪志, 有机化学, 2019, 39, 1323.)
[23] Meng, G.; Mou, J.; Chen, R.; Wang, M.; Hong, Z. Chin. J. Org. Chem. 2012, 32, 2378(in Chinese). (孟光荣, 李嘉俊, 张倩, 马红梅, 有机化学, 2012, 32, 2378.)
[24] Arvela, R. K.; Leadbeater, N. E. Org. Lett. 2005, 7, 2101.
[25] Anderson, K. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2005, 44, 6173.
[26] Wang, C.; Mu, C.; Xiang, J.; Wang, B.; Zhang, C.; Song, J.; Wen, F. Chin. J. Chem. 2018, 36, 157.
[27] Li, X.; Wang, W.; Li, R.; Zhang, P.; Chen, H. Chin. J. Org. Chem. 2012, 32, 1519(in Chinese). (李小六, 王玮, 李锐, 张平竹, 陈华, 有机化学, 2012, 32, 1519.)
[28] Kokel, A.; Schäfer, C.; Török, B. Green Chem. 2017, 19, 3729.
[29] Fan, W.; Yang, Z.; Jiang, B.; Li G. Org. Chem. Front. 2017, 4, 1091.
[30] Liu, C.-R.; Ding, L.-H. Org. Biomol. Chem. 2015, 13, 2251.
Options
文章导航

/

〈 〉