Efficient Construction of Carbazole Derivatives via New Benzyne Precursors of Four Acetylene Modules
Received date: 2015-05-23
Online published: 2015-11-19
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21272088, 21472059, 21402057) and the Program for Academic Leader in Wuhan Municipality (No. 201271130441).
Benzyne is one of very important reactive intermediates in organic synthesis, and has been comprehensively utilized as a building block in organic synthesis. However, traditional synthetic methods need to use harsh reaction condition, which has limited its practical application. With the emergence of moderate preparation method, benzyne has attracted considerable attentions from synthetic chemists. Latest results indicate that benzyne can be effectively generated by using some special intermediates containing three or four acetylene motifs, which called the hexadehydro-Diels-Alder (HDDA) reaction. This thermal cycloisomerization of a triyne precursor constitutes a reagent and byproduct free method for making benzyne intermediates of considerable structural complexity. On the other hand, carbazole and its derivatives is one very important type of nitrogen-containing aromatic heterocyclic compounds. They are used as pharmaceuticals, agrochemicals, dyes, pigments, light-emitting photosensizer, charge/hole transport material and photovoltaic and display devices, etc. Various functional groups can be easily introduced into carbazole ring through structural modification. Develop new synthetic methodology for the synthesis of carbazole and its derivatives is very important. In this paper, we took advantage of the hexadehydro Diels-Alder reaction of bis-1,3-diynes to generate arynes and used them for an intramolecular nucleophile addition reaction to generate various carbazole derivatives. A series of four acetylene-containing compounds were synthesized through the corresponding Cadiot-Chodkiewicz coupling reaction in good yields. The corresponding carbazole derivatives were received in good yields after heating benzyne precursors of four acetylene modules in toluene at 90 ℃ for 5 h. These reaction exhibited very high efficiency as well as wide substrate scope. In addition, we found that the carbazole ring and indole ring were formed simultaneously in one step with using AgNO3 as catalyst. The possible mechanism of corresponding N—H insertion reaction involves AgNO3 as a catalyst was proposed. This strategy provides a new way for the synthesis of heterocyclic compounds.
Chen Zhao , Shan Wei , Yin Jun , Yu Guangao , Liu Shenghua . Efficient Construction of Carbazole Derivatives via New Benzyne Precursors of Four Acetylene Modules[J]. Acta Chimica Sinica, 2015 , 73(10) : 1007 -1012 . DOI: 10.6023/A15050353
[1] Wang, D. W.; Lin, H. Y.; Cao, R. J.; Yang, S. G.; Chen, T.; He, B.; Chen, Q.; Yang, W. C.; Yang, G. F. Acta Chim. Sinica 2015, 73, 29. (王大伟, 林红艳, 曹润洁, 杨盛刚, 陈涛, 何波, 陈琼, 杨文超, 杨光富, 化学学报, 2015, 73, 29.)
[2] Wang, X. W.; Chen, S. Acta Chim. Sinica 2014, 72, 1147. (王晓伟, 陈莎, 化学学报, 2014, 72, 1147.)
[3] Zhang, X.; Lv, Y. H.; Li, Y.; Xiong, T.; Zhang, Q. Acta Chim. Sinica 2014, 72, 1139. (张茜, 吕允贺, 李燕, 熊涛, 张前, 化学学报, 2014, 72, 1139.)
[4] Tan, F.; Chen, J. R.; Wang, P.; Xiao, W. J. Acta Chim. Sinica 2014, 72, 836. (谭芬, 陈加荣, 王萍, 肖文精, 化学学报, 2014, 72, 836.)
[5] Zhang, L.; Lin, Y.; Wang, J.; Zhu, X. L.; Yao, Q. L.; Yao, Q. Z. Chin. J. Org. Chem. 2015, 35, 497. (张磊, 林娅, 王京, 朱心玲, 姚秋丽, 姚其正, 有机化学, 2015, 35, 497.)
[6] Chen, B.; Yu, C. J.; Zhang, G. Z. Chin. J. Org. Chem. 2015, 35, 625. (陈斌, 于丛军, 张国柱, 有机化学, 2015, 35, 625.)
[7] Zhang, R. B.; Lu, J. R.; Xin, C. W.; Liu, J. B.; Mu, J. B.; Yang, X. Y.; Wang, H. Y.; Wang, M. J.; Zhang, H. Chin. J. Org. Chem. 2015, 35, 858. (张瑞波, 卢俊瑞, 辛春伟, 刘金彪, 穆江蓓, 杨旭云, 王宏韫, 王美君, 张贺, 有机化学, 2015, 35, 858.)
[8] Liu, L.; Guo, Q.; Li, J.; Yao, B.; Tian, W. Chin. J. Chem. 2013, 31, 456.
[9] Han, L. Z.; Wang, Z.; Hua, Y. J.; Ren, A. M.; Liu, Y. L.; Liu, P. J. Acta Chim. Sinica 2012, 70, 579. (韩立志, 王卓, 华英杰, 任爱民, 刘艳玲, 刘朋军, 化学学报, 2012, 70, 579.)
[10] Kim, D.; Lee, J. K.; Kang, S. O.; Ko, J. Tetrahedron 2007, 63, 1913.
[11] Song, S. Y.; Jang, M. S. Macromolecules 1999, 32, 1482.
[12] Huang, J.; Niu, Y. H.; Yang, W.; Hou, Q.; Xu, Y. S.; Yuan, M.; Cao, Y. Acta Chim. Sinica 2003, 61, 765. (黄剑, 牛于华, 杨伟, 侯琼, 许怡赦, 袁敏, 曹镛, 化学学报, 2003, 61, 765.)
[13] Smitrovich, J. H.; Davies, I. W. Org. Lett. 2004, 6, 533.
[14] Choi, T. A.; Czerwonka, R.; Frohner, W.; Krahl, M. P.; Reddy, K. R.; Franzblau, S. G.; Knolker, H.-J. ChemMedChem. 2006, 1, 812.
[15] Liu, Z.; Larock, R. C. Org. Lett. 2004, 6, 3739.
[16] Bedford, R. B.; Betham, M. J. Org. Chem. 2006, 71, 9403.
[17] Liu, Z.; Larock, R. C. Tetrahedron 2007, 63, 347.
[18] Nozaki, K.; Takahashi, K.; Nakano, K.; Hiyama, T.; Tang, H.-Z.; Fujiki, M.; Yamaguchi, S.; Tamao, K. Angew. Chem., Int. Ed. 2003, 42, 2051.
[19] Witulski, B.; Alayrae, C. Angew. Chem., Int. Ed. 2002, 41, 3281.
[20] Peter Tsang, W. C.; Zheng, N.; Buehwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560.
[21] Park, J.; Yan, M. Acc. Chem. Res. 2013, 46, 181.
[22] Bhunia, A.; Yetra, S. R.; Biju, A. T. Chem. Soc. Rev. 2012, 41, 3140.
[23] Mao, K. B.; Fu, X. P.; Liu, D.; Li, S.; Liu, Y. H. Chin. J. Org. Chem. 2013, 33, 780. (毛可彬, 付晓平, 刘丹, 李石, 刘元红, 有机化学, 2013, 33, 780.)
[24] Chen, Z.; Liang, J.; Yin, J.; Yu, G.-A.; Liu, S. H. Tetrahedron Lett. 2013, 54, 5785.
[25] Siyang, H. X.; Wu, X. R.; Liu, H. L.; Wu, X. Y.; Liu, P. N. J. Org. Chem. 2014, 79, 1505.
[26] Pian, J.-X.; He, L.; Du, G.-F.; Guo, H.; Dai, B. J. Org. Chem. 2014, 79, 5820.
[27] Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211.
[28] Hoye, T. R.; Baire, B.; Niu, D.; Willoughby, P. H.; Woods, B. P. Nature 2012, 490, 208.
[29] Karmakar, R.; Yun, S. Y.; Wang, K. P.; Lee, D. Org. Lett. 2014, 16, 6.
[30] Hoye, T. R.; Baire, B.; Wang, T. Chem. Sci. 2014, 5, 545.
[31] Niu, D.; Wang, T.; Woods, B. P.; Hoye, T. R. Org. Lett. 2014, 16, 254.
/
| 〈 |
|
〉 |
