Chinese Journal of Organic Chemistry >
Study of the Friedel-Crafts Reaction of Cyanuric Chloride with Low-Boiling Aromatic Ring
Received date: 2017-04-17
Revised date: 2017-05-22
Online published: 2017-06-16
Supported by
Project supported by the Scientific Research Foundation of the Education Department of Sichuan Province (No.12ZB128) and the Key Research Fund Program of Xihua University (No.Z1123328).
The cyanuric chloride and benzene Friedel-Crafts arylation using Lewis acid catalyst in high pressure autoclave was studied in this manuscript. The aim compounds 2,4-dichloro-6-phenyl-1,3,5-triazine and 2,4,6-triphenyl-1,3,5-triazine could be got with high selectivity and yields by varying reaction temperature, substrate and catalyst amount, which application was expecting and promising. The transition state was obtained by quantum calculation density functional theory (DFT) method using Gaussian software, and the experimental results and mechanism of this reaction were discussed from the point of dynamics and thermo-dynamics.
Zou Hao , Wang Xueding , Yang Weiqing , Zhang Yuanyuan , Chen Hua , Wang Yuliang , Ma Menglin , Du Quan . Study of the Friedel-Crafts Reaction of Cyanuric Chloride with Low-Boiling Aromatic Ring[J]. Chinese Journal of Organic Chemistry, 2017 , 37(10) : 2697 -2704 . DOI: 10.6023/cjoc201704027
[1] (a) Suda, A.; Kawasaki, K.; Komiyama, S.; Isshiki, Y.; Yoon, D. O.; Kim, S. J.; Na, Y. J.; Hasegawa, K.; Fukami, T. A.; Sato, S. Bioorg. Med. Chem. 2014, 22, 892.
(b) Zhou, J.; Min, J.; Li, Z. G.; Anne, Y.; Heather, D.; Tian, G.; Young-Tae, C.; Neville, R. K. Bioorg. Med. Chem. Lett. 2008, 18, 1308.
(c) Sergio, M.; Davide, P.; Paolo, C.; Nicoletta, B.; Diego, M. ChemMedChem 2008, 3, 873.
(d) Rita, M.; Simona, S.; Giovanni, S.; Francesca, V.; Lisa, D. V. J. Med. Chem. 2004, 47, 4649.
(e) Nishimura, N.; Kato, A.; Maeba, I. Carbohydr. Res. 2001, 331, 77.
(f) Klenke, B.; Stewart, M.; Barrett, M. P.; Brun, R.; Gilbert, I. H. J. Med. Chem. 2001, 44, 3440.
(g) Iino, Y.; Karakida, T.; Sugamata, N.; Andoh, H.; Takei, H.; Takahashi, M.; Yaguchi, S.; Matsuno, T.; Takehara, M.; Sakato, M.; Kawashima S.; Morishita, Y. Anticancer Res. 1998, 18, 171.
(h) Li, Y. J.; Shi, X. L.; Gao, L. X.; Jin, K.; Sheng, L.; Wu, J. H.; Peng, L. N.; Li, J. Chin. J. Org. Chem. 2015, 35, 191(in Chinese). (李英俊, 史相玲, 高立信, 靳焜, 盛丽, 吴疆红, 彭立娜, 李佳, 有机化学, 2015, 35, 191.)
[2] (a) Naik, S.; Kumaravel, M.; Mague, J. T.; Balakrishna, M. S. Inorg. Chem. 2014, 53, 1370.
(b) Xiao, C. Y.; Li, Y. M.; Lun, H. J.; Cui, C. Y.; Xu, Y. Q. J. Solid State Chem. 2013, 208, 127.
[3] Wojciech, C.; Joanna, P.; Roland, S.; Mariola, K.; Edyta, G. Dyes Pigm. 2006, 71, 224.
[4] (a) Roy, B.; De, N.; Majumdar, K. C. Chem. Eur. J. 2012, 18, 14560.
(b) Majumdar, K. C.; De, N.; Roy, B.; Bhowmik, A. Liq. Cryst. 2010, 37, 1459.
(c) Kotha, S.; Kashinath, D.; Kumar, S. Tetrahedron Lett. 2008, 49, 5419.
(d) Lee, C. H.; Yamamoto, T. Bull. Chem. Soc. Jpn. 2002, 75, 615.
(e) Goldmann, D.; Janietz, D.; Schmidt, C.; Wendroff, J. H. Angew. Chem., Int. Ed. 2000, 39, 1851.
[5] (a) Hernandez-Juarez, M.; Vaquero, M.; Alvarez, E.; Salazar, V.; Suarez, A. Dalton Trans. 2013, 42, 351.
(b) Santra, P. K.; Sagar, P. J. Mol. Catal. A:Chem. 2003, 197, 37.
[6] Wang, G. R.; Zeng, H. P. Chin. J. Org. Chem. 2009, 29, 1115(in Chinese). (王光荣, 曾和平, 有机化学, 2009, 29, 1115.)
[7] Luo, H. M.; Wang, H.; Zeng, Z.; Zeng, H. P. Chin. J. Org. Chem. 2013, 33, 916(in Chinese). (罗浩敏, 王辉, 曾卓, 曾和平, 有机化学, 2013, 33, 916.)
[8] Hirt, R.; Nidecker, H.; Berchtold, R.; Schönholzer, G. Helv. Chim. Acta 1950, 33, 1365.
[9] (a) Janietz, D.; Bauer, M. Synthesis 1993, 33.
(b) Isfahani, A. L.; Mohammadpoor-Baltork, I.; Mirkhani, V.; Khosropour, A. R.; Moghadam, M.; Tangestaninejad, S.; Kia, R. Adv. Synth. Catal. 2013, 355, 957.
[10] Forsberg, J. H.; Spaziano, V. T.; Klump, S. P.; Sanders, K. M. J. Heterocycl. Chem. 1988, 25, 767.
[11] Biswas, S.; Batra, S. Eur. J. Org. Chem. 2012, 18, 3492.
[12] Xie, F.; Chen, M.; Wang, X.; Jiang, H.; Zhang, M. Org. Biomol. Chem. 2014, 12, 2761.
[13] Guo, W. Org. Biomol. Chem. 2015, 13, 10285.
[14] Huang, W.; Tang, F. S.; Li, B.; Su, J. H.; Tian, H. J. Mater. Chem. 2014, 6, 1141.
[15] Conn, G.; Eisler, S. Org. Lett. 2011, 13, 5080.
[16] (a) Bernhard, M.; Gerhard, Z. US 5322941, 1994[Chem. Abstr. 1994, 121, 157678].
(b) Hou, B. Mod. Plast. Process. Appl. 2002, 14, 24(in Chinese). (侯博, 现代塑料加工应用, 2002, 14, 24.)
[17] Ishikawa, M.; Yamazaki, Y.; Koyama, T. J. Ind. Chem. 1970, 73, 550.
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