Chinese Journal of Organic Chemistry >
Syntheses and Spectral Properties of N-Alkyl-5-arylindole-3-carboxaldehydes
Received date: 2014-07-09
Revised date: 2014-09-28
Online published: 2014-10-22
Supported by
Project supported by the University Student Innovative Program of Guangdong Province (No. 1055912003).
Using 5-bromoindole as raw material and PdCl2(dppf) as catalyst, N-alkyl-5-arylindole-3-carboxaldehydes were synthesized by the formylation, alkylation and Suzuki coupling reaction. The effects of catalysts, alkali reagents, solvents and the molar ratio of reactants on Suzuki coupling reaction have been surveyed. UV-Vis and fluorescence spectra of the title compounds in acetonitrile were also investigated.
Lin Zhiqiang , Zeng Xiangchao , Meng Yuxia . Syntheses and Spectral Properties of N-Alkyl-5-arylindole-3-carboxaldehydes[J]. Chinese Journal of Organic Chemistry, 2015 , 35(2) : 490 -496 . DOI: 10.6023/cjoc201407011
[1] Tiwari, R. K.; Singh, D.; Singh, J.; Yadav, V.; Pathak, A. K.; Dabur, R.; Chhillar, A. K.; Singh, R.; Sharma, G. L.; Chandra, R.; Verma, A. K. Bioorg. Med. Chem. Lett. 2006, 16, 413.
[2] Zhai, X.; Fang, Y.-Y.; Leng, X.; Ma, C.-L.; Zeng, L.-L.; Gong, P. Chin. J. Med. Chem. 2008, (4), 254 (in Chinese). (翟鑫, 房元英, 冷雪, 马崇雷, 曾兰兰, 宫平, 中国药物化学杂志, 2008, (4), 254.)
[3] Tiwari, R. K.; Verma, A. K. Bioorg. Med. Chem. Lett. 2006, 14, 2747.
[4] Chen, L.-R.; Wang, Y.-C.; Lin, Y.-W.; Chou, S.-Y.; Chen, S.-F.; Liu, L.-T.; Wu, Y.-T.; Kuo, C.-J.; Chen, T.-S.; Juang, S.-H. Bioorg. Med. Chem. Lett. 2005, 15, 3058.
[5] Giampieri, M.; Balbi, A.; Mazzei, M.; Colla, P. L.; Ibba, C.; Loddo, R. Antiviral Res. 2009, 83, 179.
[6] Dahlhaus, J.; Georgi, G.; Mueller, J. D. DE 10124600, 2002 [Chem. Abstr. 2002, 137, 386319].
[7] Staub, R. E.; Feng, C.; Onisko, B.; Bailey, G. S.; Firestone, G. L.; Bjeldanes, L. F. Chem. Res. Toxicol. 2002, 15, 101.
[8] Xu, M.-H.; Zhang, G.-Y.; Xie, Z.-X.; He, C.-M. Chin. J. Digestion 2002, 10, 6052 (in Chinese). (徐美华, 张桂英, 谢兆霞, 何春梅, 中华消化杂志, 2002, 10, 6052.)
[9] James, D. A.; Koya, K.; Li, H.; Liang, G.; Xia, Z.; Ying, W.; Wu, Y.; Sun, L. Bioorg. Med. Chem. Lett. 2008, 18, 1784.
[10] Duan, C.-F.; Yang, Y.-J. Acta Pharm. Sin. 1996, 31, 182 (in Chinese). (段传风, 杨依军, 药学学报, 1996, 31, 182.)
[11] Horiuchi, T.; Miura, H.; Uehida, S. Chem. Commun. 2003, 24, 3036.
[12] Horiuchi, T.; Miura, H.; Sumioka, K.; Uchida, S. J. Am. Chem. Soc. 2004, 126, 12218.
[13] Zhan, W.-S.; Pan, S.; Li, Y.-Z.; Chen, M.-D. Acta Phys.-Chim. Sin. 2009, 25, 2087 (in Chinese). (詹卫伸, 潘石, 李源作, 陈茂笃, 物理化学学报, 2009, 25, 2087.)
[14] Ge, Y.-H.; Wu, Y.-M.; Xue, Z.-J. Chin. J. Org. Chem. 2006, 26, 563 (in Chinese). (葛裕华, 吴亚明, 薛忠俊, 有机化学, 2006, 26, 563.)
[15] Da, B.-L. Flavour Fragrance Cosmetics 1995, 28, 22 (in Chinese). (笪宝林, 香料香精化妆品, 1995, 28, 22.)
[16] Zhang, R.; Li, J.-T.; Fu, C.-L.; Luo, X.-T. Mater. Rev. 2011, 25, 61 (in Chinese). (张蓉, 李锦堂, 傅翠梨, 罗学涛, 材料导报, 2011, 25, 61.)
[17] Yu, K.; Guan, S.-X.; Zhang, H.-W.; Zhou, B.-B.; Li, L. Nat. Sci. J. Harbin Normal Univ. 2006, 22, 70 (in Chinese). (于凯, 关淑霞, 张宏伟, 周百斌, 李玲, 哈尔滨师范大学自然科学学报, 2006, 22, 70.)
[18] Kiliç, Z.; Isgör, Y. G.; Ölgen, S. Arch. Pharm. 2009, 342, 333.
[19] Go, M. L.; Leow, J. L.; Gorla, S. K.; Schüller, A. P.; Wang, M.; Casey, P. J. J. Med. Chem. 2010, 53, 6838.
[20] Winter-Vann, A. M.; Baron, R. A.; Wong, W.; Dela C. J.; York, J. D.; Gooden, D. M.; Bergo, M. O.; Young, S. G.; Toone, E. J.; Casey, P. J. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 4336.
[21] Valdenaire, A.; Pothier, J.; Renneberg, D.; Riederer, M. A.; Peter, O.; Leroy, X.; Gnerre, C.; Fretz, H. Bioorg. Med. Chem. Lett. 2013, 23, 944.
[22] Li, Q. Q.; Zou, J. H.; Chen, J. W.; Liu, Z. J.; Qin, J. G.; Li, Z.; Cao, Y. Phys. Chem. B 2009, 113, 5816.
[23] Lo, K. K.-W.; Chung, C.-K.; Zhu, N.-Y. Chem. Eur. J. 2003, 9, 475.
[24] Chen, F.-F.; Bian, Z.-Q.; Liu, Z.-W.; Nie, D.-B. Chen, Z.-Q.; Huang, C.-H. Inorg. Chem. 2008, 47, 2507.
[25] Martin, A. R.; Yang, Y. Acta Chem. Scand. 1993, 47, 221.
[26] Wallow, T. I.; Novak, B. M. J. Org. Chem. 1994, 59, 5034.
[27] Gronowitz, S.; Hörnfeldt, A. B.; Yang, Y. H. Chem. Scr. 1988, 28, 281.
[28] Zhang, H.; Kwong, F. Y.; Tian Y.; Chan, K. S. J. Org. Chem. 1998, 63, 6886.
[29] Gao, F.-Q.; He, H.-J.; Wang, X.-M.; Guo, Q. Fine Chem. 2012, 29, 1142 (in Chinese). (高丰琴, 何汉江, 王小明, 郭强, 精细化工, 2012, 29, 1142.)
[30] Xin, B.-W. Chin. J. Appl. Chem. 2008, 25, 895 (in Chinese). (辛炳炜, 应用化学, 2008, 25, 895.)
[31] DeVasher, R. B.; Moore, L. R.; Shaughnessy, K. H. J. Org. Chem. 2004, 69, 7919.
[32] Bumagin, N. A.; Korolev, D. N. Tetrahedron Lett. 1999, 40, 3057.
[33] Mao, P.; Yang, L.-R.; Liu, X.-J.; Cai, Y.-J.; Zhao, C.-L.; Song, M.-P. Chin. J. Org. Chem. 2011, 31, 1828 (in Chinese). (毛璞, 杨亮茹, 刘秀君, 蔡雅静, 赵成磊, 宋毛平, 有机化学, 2011, 31, 1828.)
[34] Haruaki, I; Kazuaki, Y; Jun'ichi, K. Tetrahetron 2012, 68, 6186.
[35] Zhang, W.; Jin, X.-L.; Yu, X.-G.; Zhou, J.; Tang, G.-P.; Peng, D.-H.; Hu, J.-M.; Zhong, C.-F. J. Organomet. Chem. 2014, 749, 26.
/
〈 |
|
〉 |