高温水中2-甲基喹啉及2-甲基吡啶与芳醛的反应研究
Reaction of 2-Methylquinoline and 2-Methylpyridine with Aromatic Aldehydes in High Temperature Water
Received date: 2016-12-25
Revised date: 2017-03-29
Online published: 2017-04-18
肖尚友 , 毕旌富 , 穆小静 , 周曌 , 徐广 . 高温水中2-甲基喹啉及2-甲基吡啶与芳醛的反应研究[J]. 有机化学, 2017 , 37(8) : 2159 -2164 . DOI: 10.6023/cjoc201612058
Alkyl aza-arene derivatives were synthesized in high-temperature water without catalyst. The effects of temperature, reaction time, molar ratio of reactants and amount of water on the reaction were investigated. The results indicate that it is an efficient way to synthesize 2-methylquinoline derivatives and 2-methylpyridine derivatives from 2-methylquinoline and 2-methylpyridine with various aromatic aldehydes by C－H bond activation. This process is clean and easy to operate.
[1] Li, C. J.; Chen, L. Chem. Soc. Rev. 2006, 35, 68.
[2] Dallinger, D.; Kappe, C. O. Chem. Rev. 2007, 107, 2563.
[3] Simon, M. O.; Li, C. J. Chem. Soc. Rev. 2012, 41, 1415.
[4] El-Batta, A.; Jiang, C. C.; Zhao, W.; Anness, R.; Cooksy, A. L.; Bergdahl, M. J. Org. Chem. 2007, 72, 5244.
[5] Xiao, S. Y.; He, Y.; Xu, G.; Liu, Q. Res. Chem. Intermed. 2015, 41, 3299.
[6] Carlsson, M.; Habenicht, C.; Kam, L. C.; Antal, M. J.; Bian, N.; Cunningham, R. J.; Jones, M. Ind. Eng. Chem. Res. 1994, 33, 1989.
[7] Zhu, Q. Y.; Shen, H. M.; Ji, H. B. Chin. J. Org. Chem. 2016, 36, 1907(in Chinese). (朱庆英, 沈海民, 纪红兵, 有机化学, 2016, 36, 1907.)
[8] Jiang, X. J.; Shen, Y. L.; Liu, Z. L.; Lu, X. L.; Tu, T. Chin. J. Org. Chem. 2015, 35, 2389(in Chinese). (蒋晓军, 申雅靓, 刘泽龙, 吕绪良, 涂涛, 有机化学, 2015, 35, 2389.)
[9] Chen, J.; Mao, J. C.; Zheng, Y. Chin. J. Org. Chem. 2015, 35, 672(in Chinese). (陈洁, 毛金成, 郑洋, 有机化学, 2015, 35, 672.)
[10] Akiya, N.; Savage, P. E. Chem. Rev. 2002, 102, 2725.
[11] Kalinichev, A. G.; Churakov, S. V. Chem. Phys. Lett. 1999, 302, 411.
[12] Mountain, R. D. J. Chem. Phys. 1999, 110, 2109.
[13] Houghton, P. J.; Woldematiam, T. Z.; Watanabe, T.; Yates, M. Planta Med. 1999, 65, 250.
[14] Michael, J. P. Nat. Prod. Rep. 2000, 17, 603.
[15] Jacquemond-Collet, I.; Benoit-Vical, F.; Mustofa; Valentin, A.; Stanislas, E.; Mallié, M.; Fourasté, I. Planta Med. 2002, 68, 68.
[16] Rueping, M.; Tolstoluzhsky, N. Org. Lett. 2011, 13, 1095.
[17] Niu, R.; Xiao, J.; Liang, T.; Li, X. W. Org. Lett. 2012, 14, 676.
[18] Qian, B.; Guo, S. M.; Shao, J. P.; Zhu, Q. M.; Yang, L.; Xia, C. G.; Huang, H. M. J. Am. Chem. Soc. 2010, 132, 3650.
[19] Burton, P. M.; Morris, J. A. Org. Lett. 2010, 12, 5359.
[20] Luo, F. H.; Long, Y.; Li, Z. K.; Zhou, X. G. Acta Chim. Sinica 2016, 74, 805(in Chinese). (罗飞华, 龙洋, 李正凯, 周向葛, 化学学报, 2016, 74, 805.)
[21] Wang, Z. L. RSC Adv. 2015, 5, 5563.
[22] Rao, N. N.; Meshram, H. M. Tetrahedron Lett. 2013, 54, 5087.
[23] Walton, A. F.; Tipson, R. S.; Cretcher, L. H. J. Am. Chem. Soc. 1945, 67, 1501.
[24] Stanek, J.; Zekja, Z. Chem. Listy 1953, 47, 749.
[25] Hey, D. H.; Osbond, J. H. J. Chem. Soc. 1949, 3164.
/
| 〈 |
|
〉 |
