Chinese Journal of Organic Chemistry >
An Efficient Synthesis of Oxime Compounds Catalyzed by Superfine Kaolin under Microwave Irradiation
Received date: 2018-11-17
Revised date: 2019-02-13
Online published: 2019-03-29
Supported by
Project supported by the Basic Public Research Project of Zhejiang Province (No. LGG18B020002).
Oxime compounds were efficiently synthesized with aromatic or aliphatic ketones and hydroxylamine hydrochloride as raw materials in the PEG-400 solution, using cheap and readily available superfine kaolin as catalyst under microwave irradiation condition. The effects of the catalyst, the solvent type, reaction time, reaction temperature on the reaction were investigated. The structures of the products were detected by melting point, nuclear magnetic resonance, infrared spectroscopy and mass spectrometry data. This method has the advantages of short reaction times (5~15 min), good yields, and simple operation as well as environmental friendliness. In addition, the preliminary experiment shows that superfine kaolin could also catalyze transoximation reaction and preparation of oxime ether compounds under microwave irradiation with the yields of 42%~67% and 59%~72%.
Key words： superfine kaolin; microwave; oxime compound; catalysis; transoximation; oxime ether compounds
Liang Ling , Mou Jialing , Chen Yue , Wang Mengsha , Hong Zhi . An Efficient Synthesis of Oxime Compounds Catalyzed by Superfine Kaolin under Microwave Irradiation[J]. Chinese Journal of Organic Chemistry, 2019 , 39(5) : 1323 -1332 . DOI: 10.6023/cjoc201811021
[1] Bolotin, D. S.; Bokach, N. A.; Demakova, M. Y.; Kukushkin, V. Y. Chem. Rev. 2017, 117, 13039.
[2] Ran, L. F.; Liang, H.; Guan, Z. H. Chin. J. Org. Chem. 2013, 33, 66(in Chinese). (冉陇飞, 梁浩, 关正辉, 有机化学, 2013, 33, 66.)
[3] Watson, K. G. Aust. J. Chem. 2011, 64, 367.
[4] Kolesnikov, A. M.; Yuidin, M. A.; Nikiforov, A. S.; Ivanov, I. M.; Vengerovich, N. G.; Makacheev, A. S. Bull. Exp. Biol. Med. 2018, 164, 624.
[5] Wang, X. B.; Chen, M. H.; Li, Q.; Zhang, J. P.; Ruan, X. H.; Xie, Y.; Xue, W. Chem. Pap. 2017, 71, 1225.
[6] Canario, C.; Silvestre, S.; Falcao, A.; Alves, G. Curr. Med. Chem. 2018, 25, 660.
[7] Patil, V. V.; Gayakwad, E. M.; Shankarling, G. S. J. Org. Chem. 2016, 81, 781.
[8] Liu, S. H.; Hao, F.; Liu, P. L.; Luo, H. A. RSC Adv. 2015, 5, 22863.
[9] Reddy, M. K.; Mallik, S.; Ramakrishna, I.; Baidya, M. Org. Lett. 2017, 19, 1694.
[10] Hong, Z.; Li, J. J.; Chen, G.; Jiang, H. J.; Yang, X. F.; Pan, H.; Su, W. K. RSC Adv. 2016, 6, 13581.
[11] Sathyanarayana, P.; Upare, A.; Ravi, O.; Muktapuram, P. R.; Bathula, S. R. RSC Adv. 2016, 6, 22749.
[12] Bezlada, A.; Szewczyk, M.; Mlynarski, J. J. Org. Chem. 2016, 81, 336.
[13] Xu, Y. Y.; Yang, Q. S.; Li, Z. H.; Gao, L. Y.; Zhang, D. S.; Wang, S. F.; Zhao, X. Q.; Wang, Y. J. Chem. Eng. Sci. 2016, 152, 717.
[14] Lin, C. K.; Cheng, L. W.; Li, H. Y.; Yun, W. Y.; Cheng, W. C. Org. Biomol. Chem. 2015, 13, 2100.
[15] Xie, F. K.; Du, C.; Pang, Y. D.; Lian, X.; Xue, C. T.; Chen, Y. Y.; Wang, X. F.; Cheng, M. S.; Guo, C.; Lin, B.; Liu, Y. X. Tetrahedron Lett. 2016, 57, 5820.
[16] Peterson, K. E.; Cinelli, M. A.; Morrell, A. E.; Mehta, A.; Dexheimer, T. S.; Agama, K.; Antony, S.; Pommier, Y.; Cushman, M. J. Med. Chem. 2011, 54, 4937.
[17] Eshghi, H.; Hassankhani, A. Org. Prep. Proced. Int. 2005, 37, 575.
[18] Sharghi, H.; Sarvari, M. H. Synlett 2001, 1, 99.
[19] Yao, Q. C.; Fan, L.; Liu, L.; Huang, Y. M.; Cui, J. G. Chem. Res. Appl. 2013, 25, 220(in Chinese). (姚秋翠, 范磊, 刘亮, 黄燕敏, 崔建国, 化学研究与应用, 2013, 25, 220.)
[20] Noverges, B.; Mollar, C.; Medio-Simón, M.; Asensio, G. Adv. Synth. Catal. 2013, 355, 2327.
[21] Manetti, F.; Magnani, M.; Castagnolo, D.; Passalacqua, L.; Botta, M.; Corelli, F.; Saddi, M.; Deidda, D.; De Logu, A. ChemMedChem 2006, 1, 973.
[22] Ghozlojeh, N. P.; Setamdideh, D. Orient. J. Chem. 2015, 31, 1823.
[23] Juskowiak, M.; Krzyzanowski, P. J. Prakt. Chem. 1989, 331, 870.
[24] Shimaoka, H.; Kuramoto, H.; Furukawa, J. I.; Miura, Y.; Kurogochi, M.; Kita, Y.; Hinou, H.; Shinohara, Y.; Nishimura, S. I. Chem.-Eur. J. 2007, 13, 1664.
[25] Sridhar, M.; Narsaiah, C.; Raveendra, J.; Reddy, G. K.; Reddy, M. K. K.; Ramanaiah, B. C. Tetrahedron Lett. 2011, 52, 4701.
[26] Hyodo, K.; Togashi, K.; Oishi, N.; Hasegawa, G.; Uchida, K. Green Chem. 2016, 18, 5788.
[27] Pienkoß, F.; Ochoa-Hernández, C.; Theyssen, N.; Leitner, W. ACS Sustainable Chem. Eng. 2018, 6, 8782.
[28] Aras, A.; Albayrak, M.; Arikan, M.; Sobolev, K. Clay Miner. 2007, 42, 233.
[29] Zheng, Y. F.; Li, D.; Chen, S. K.; Sun, S. H.; Liu, C. H.; Gao, X. H. Ind. Catal. 2012, 20, 1(in Chinese). (郑云锋, 李荻, 陈淑琨, 孙书红, 刘从华, 高雄厚, 工业催化, 2012, 20, 1.)
[30] Shen, J. X.; Ma, H. W. Bull. Chin. Ceram. Soc. 2016, 35, 1150(in Chinese). (申继学, 马鸿文, 硅酸盐通报, 2016, 35, 1150.)
[31] Yan, H. Q.; Chen, X. Q.; Wu, T. T.; Feng, Y. H.; Wang, C. X.; Li, J. C.; Lin, Q. Polym. Bull. 2014, 71, 2923.
[32] Ignatova, T.; Mincheva, K.; Ignatov, S.; Dzhelyaydinova, A.; Petkov, T.; Kyazimov, A. J. Chem. Technol. Metall. 2013, 48, 186.
[33] Liu, H. J.; Ao, L. Inner Mongolia Pet. Ind. 1998, 24, 112(in Chinese). (刘惠军, 敖丽, 内蒙古石油化工, 1998, 24, 112.)
[34] Chermahini, A. N.; Teimouri, A.; Momenbeik, F.; Zarei, A.; Dalirnasab, Z.; Ghaedi, A.; Roosta, M. J. Heterocycl. Chem. 2010, 47, 913.
[35] Maheen, G.; Tian, G.; Song, Z.; He, C.; Shi, Z.; Liu, Z.; Yuan, H.; Feng, S. J. Heterocycl. Chem. 2010, 47, 483.
[36] Hirano, M.; Monobe, H.; Yakabe, S.; Morimoto T. J. Chem. Res., Synop. 1998, 0, 662.
[37] Matsuzaki, T.; Ohsuga, K.; Sugi, Y.; Takami, Y.; Imamura, J. J. Chem. Soc. Jpn., Chem. Ind. Chem. 1985, 12, 2331.
[38] Roudier, J. F.; Foucaud, A. Tetrahedron Lett. 1984, 25, 4375.
[39] Kappe, C. O.; Pieber, B.; Dallinger, D. Angew. Chem., Int. Ed. 2013, 52, 1088.
[40] Nuechter, M.; Ondruschka, B.; Bonrath, W.; Gum, A. Green Chem. 2004, 6, 128.
[41] Alam, M.; Lee, D. U. Korean J. Chem. Eng. 2015, 32, 1142.
[42] Erdogan, T.; Erdogan, F. O. Lett. Org. Chem. 2018, 15, 99.
[43] Khan, A. U.; Avecillia, F.; Malik, N.; Khan, M. S.; Khan, M. S.; Mushtaque, M. J. Mol. Struct. 2016, 1122, 100.
[44] Gedye, R. N.; Smith, F. E.; Westaway, K. C. Can. J. Chem., 1988, 66, 17.
[45] Lu, C. B. China Pulp Pap. Ind. 2017, 38, 11(in Chinese). (路崇斌, 中华纸业, 2017, 38, 11.)
[46] Lapides, I.; Yariv, S.; Lahav, N. Clay Miner. 1995, 30, 287.
[47] Gu, T.; Zou, Z. G. B. Bull. Chin. Ceram. Soc. 2005, 4, 70(in Chinese). (顾涛, 邹正光, 硅酸盐通报, 2005, 4, 70.)
[48] Tian, J. Crystal Chemistry of Silicate, Wuhan University Press, Wuhan, 2010, pp. 194~196(in Chinese). (田键, 硅酸盐晶体化学, 武汉大学出版社, 武汉, 2010, pp. 194~196.)
[49] Xiong, W.; Liu, J.; Huang, N.; Zhang, H. P. J. Shaoyang Univ. (Nat. Sci. Ed.) 2012, 9, 75(in Chinese). (熊文, 刘静, 黄娜, 张红萍, 邵阳学院学报(自然科学版), 2012, 9, 75.)
[50] Lieberman, S. V. J. Am. Chem. Soc. 1955, 77, 1114.
[51] Zhukovskaya, N. A.; Dikusar, E. A. Russ. J. Org. Chem. 2010, 46, 180.
[52] Ngwerume, S.; Camp, J. E. J. Org. Chem. 2010, 75, 6271.
[53] Fazaeli, R.; Tangestaninejad, S.; Aliyan H. Catal. Commun. 2007, 8, 205.
[54] Chen, J. B.; Liu, E. M.; Chern, T. R.; Yang, C. W.; Lin, C. I.; Huang, N. K.; Lin, Y. L.; Chern, Y.; Lin, J. H.; Fang, J. M. ChemMedChem 2011, 6, 1390.
[55] Wiley, R. H.; Wakefield, B. J. J. Org. Chem. 1960, 25, 546.
[56] Mokhtari, J.; Naimi-Jamal, M. R.; Hamzeali, H.; Dekamin, M. G.; Kaupp, G. ChemSusChem 2009, 2, 248.
[57] Corma, A.; Garcia, H.; Leyva, A. J. Mol. Catal. A-Chem. 2005, 230, 97.
[58] Wang, H. Y.; Mueller, D. S.; Sachwani, R. M.; Londino, H. N.; Anderson, L. L. Org. Lett. 2010, 12, 2290.
[59] Balogh, A.; Kovendi, A.; Rotaru, D.; Craciunescu, E. US 3117995, 1964[Chem Abstr. 1964, 60, 52549].
[60] Prateeptongkum, S.; Jovel, I.; Jackstell, R.; Vogl, N.; Weckbecker, C.; Beller, M. Chem. Commun. 2009, 1990.
[61] Talapatra, S. K.; Chaudhuri, P.; Talapatra, B. Heterocycles 1980, 14, 1279.
[62] Domnin, N. A.; Yakimovich, S. I. Zh. Neorg. Khim. 1965, 1, 1024.
[63] Jain, N.; Kumar, A.; Chauhan, S. M. S. Tetrahedron Lett. 2005, 46, 2599.
[64] Gunatilaka, A. A. L.; Ramachandran, S. Indian J. Chem. 1978, 16B, 432.
[65] Bruton, E. A.; Brammer, L.; Pigge, F. C.; Aakeroey, C. B.; Leinen, D. S. New J. Chem. 2003, 27, 1084.
[66] Bodor, N.; Fey, L.; Kovendi, A. Rev. Roum. Chim. 1966, 11, 405.
[67] Dubost, E.; Fossey, C.; Cailly, T. Rault, S.; Fabis, F. J. Org. Chem. 2011, 76, 6414.
/
| 〈 |
|
〉 |
