Chinese Journal of Organic Chemistry >
Microwave-Assisted Synthesis of 3-Substituted Indole Derivatives via Three-Component Domino Reaction
Received date: 2017-09-21
Revised date: 2017-11-09
Online published: 2017-12-01
Supported by
Project supported by the National Natural Science Foundation of China (No. 21502074), the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (No. 15KJA150006) and the College Students Practice Innovation Training Plan of Jiangsu Province (No. 201711463010Z).
The research of indoles has been one of the most active areas of heterocyclic chemistry. In particular, 3-substituted indole derivatives have received much attention as building blocks for the synthesis of many natural products and other biologically active compounds. In this article, an synthetic procedure for multi-substituted indole derivatives was successfully developed by a three-component reaction of phenylglyoxal monohydrate, aromatic amine and 4-hydroxycoumarin with a catalytic amount of trifluoroacetic acid under microwave irradiation conditions. This method has the advantages of simple operation, readily available raw materials, and high atom utilization.
Key words： indole; synthesis; three-component reaction; microwave
Lin Wei , Hu Xiuxiu , Wang Yazhen , Song Shuai , Zhang Mengye , Shi Daqing . Microwave-Assisted Synthesis of 3-Substituted Indole Derivatives via Three-Component Domino Reaction[J]. Chinese Journal of Organic Chemistry, 2018 , 38(4) : 855 -862 . DOI: 10.6023/cjoc201709033
[1] (a) Houlihan, W. J.; Remers, W. A.; Brown, R. K. Indoles:Part I, Wiley, New York, 1992.
(b) Sundberg, R. J. The Chemistry of Indoles, Academic, New York, 1996.
[2] Chen, I.; Safe, S.; Bjeldanes, L. Biochem. Pharm. 1996, 51, 1069.
[3] Suzen, S.; Buyukbingol, E. Farmaco 2000, 55, 246.
[4] (a) Suzen, S.; Buyukbingol, E. Farmaco 1998, 53, 52.
(b) Buyukbingol, E.; Suzen, S.; Klopman, G. Farmaco 1994, 49, 443.
[5] Walter, G.; Liebl, R.; von Angerer, E. J. Steroid Biochem. Mol. Biol. 2004, 88, 409.
[6] (a) Giagoudakis, G.; Markantonis, S. L. Pharmacotherapy 2005, 25, 18.
(b) Ge, X.; Yannai, S.; Rennert, G.; Gruener, N.; Fares, F. A. Biochem. Biophys. Res. Commun. 1996, 228, 153.
[7] Zhu, S.; Xu, L. B.; Wang, L.; Xiao, J. Chin. J. Org. Chem. 2016, 36, 927(in Chinese). (朱帅, 徐鲁斌, 王亮, 肖建, 有机化学, 2016, 36, 927.)
[8] Somei, M.; Yamada, F. Nat. Prod. Rep. 2004, 21, 278.
[9] (a) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.
(b) Cacchi, S.; Fabrizi, G. Chem. Rev. 2011, 111, 215.
(c) Jiang, J. Z.; Wang, Y. Chin. J. Org. Chem. 2006, 26, 1025(in Chinese). (蒋金芝, 王艳, 有机化学, 2006, 26, 1025.)
[10] (a) Fischer, E.; Jourdan, F. Ber. Dtsch. Chem. Ges. 1883, 16, 2241.
(b) Fischer, E.; Hess, O. Ber. Dtsch. Chem. Ges. 1884, 17, 559.
(c) Müller, S.; Webber, M. J.; List, B. J. Am. Chem. Soc. 2011, 133, 18534.
(d) Zhao, D.; Shi, Z.; Glorius, F. Angew. Chem., Int. Ed. 2013, 52, 12426.
[11] (a) Würtz, S.; Rakshit, S.; Neumann, J. J.; Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2008, 47, 7230.
(b) Bernini, R.; Fabrizi, G.; Sferrazza, A.; Cacchi, S. Angew. Chem., Int. Ed. 2009, 48, 8078.
(c) Wei, Y.; Deb, I.; Yoshikai, N. J. Am. Chem. Soc. 2012, 134, 9098.
(d) Shi, Z.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 9220.
[12] (a) Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474.
(b) Shi, Z.; Zhang, C.; Li, S.; Pan, D.; Ding, S.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 4572.
(c) Stuart, D. R.; Alsabeh, P.; Kuhn, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 18326.
(d) Huestis, M. P.; Chan, L.; Stuart, D. R.; Fagnou, K. Angew. Chem., Int. Ed. 2011, 50, 1338.
(e) Wang, H.; Grohmann, C.; Nimphius, C.; Glorius, F. J. Am. Chem. Soc. 2012, 134, 19592.
(f) Liu, B.; Song, C.; Sun, C.; Zhou, S.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 16625.
[13] (a) Hamide, H. P.; Kurosh, R. M.; Leila, Y. M. Tetrahedron Lett. 2014, 70, 1780.
(b) Liang, Y. R.; Chen, X. Y.; Wu, Q. W.; Lin, X. F. Tetrahedron Lett. 2015, 71, 616.
(c) Han, Y.; Sheng, Y. J.; Yan, C. G. Org. Lett. 2014, 16, 2654.
(d) Guo, R. Y.; An, Z. M.; Mo, L. P.; Wang, R. Z.; Liu, H. X.; Wang, S. X.; Zhang, Z. H. ACS Comb. Sci. 2013, 15, 557.
(e) Rahmati, A.; Kenarkoohi, T.; Khavasi, H. R. ACS Comb. Sci. 2012, 14, 657.
(f) Liu, X.; Xu, X.; Wang, X.; Yang, W.; Qian, Q.; Zhang, M.; Song, L.; Deng, H.; Shao, M. Tetrahedron Lett. 2013, 54, 4451.
(g) Liu, Y. Y.; Zhang, Y.; Hu, C. F.; Wan, J. P.; Wen, C. P. RSC Adv. 2014, 4, 35528.
(h) Brahmachari, G.; Das S. RSC Adv. 2014, 4, 7380.
(i) Khan, F. A. K.; Zaheer, Z.; Sangshetti, J. N.; Patil, R. H.; Farooqui, M. Bioorg. Med. Chem. Lett. 2017, 27, 567.
(j) Balwe, S. G.; Lim, K. T.; Cho, B. G.; Jeong, Y. T. Tetrahedron 2017, 73, 3564.
(k) Kumar, S. A.; Kumar, S.; Ahmed, N. RSC Adv. 2016, 6, 108105.
(l) Wei, J.; Liu, L.; Tang, D. N.; Wu, C. P. Zhao, X. J.; Hao, W. J.; Jiang, B. J. Heterocycl. Chem. 2017, 54, 3403.
[14] (a) Fukuyama, H.; Chen, X.; Peng, G. J. Am. Chem. Soc. 1994, 116, 3127.
(b) Saito, A.; Kanno, A.; Hanzawa, Y. Angew. Chem., Int. Ed. 2007, 46, 3931.
(c) Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 3676.
(d) Sun, K.; Liu, S.; Bec, P. M.; Driver, T. G. Angew. Chem., Int. Ed. 2011, 50, 1702.
(e) Yao, B.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed. 2012, 51, 12311.
(f) Breazzano, S. P.; Poudel, Y. B.; Boger, D. L. J. Am. Chem. Soc. 2013, 135, 1600.
(g) Shan, D.; Gao, Y.; Jia, Y. Angew. Chem., Int. Ed. 2013, 52, 4902.
(h) Sagadevan, A.; Ragupathi, A.; Hwang, K. C. Angew. Chem., Int. Ed. 2015, 54, 13896.
(i) Tong, S.; Xu, Z.; Mamboury, M.; Wang, Q. Angew. Chem., Int. Ed. 2015, 54, 11809.
(j) Yan, H.; Wang, H.; Li, X.; Xin, X.; Wang, C.; Wan, B. Angew. Chem., Int. Ed. 2015, 54, 10613.
/
| 〈 |
|
〉 |
