One-Pot Synthesis of O-Arylsulfonyl Arylaldoximes under Ultrasound Irradiation

doi:10.6023/cjoc201304002

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (9): 1965-1969.DOI: 10.6023/cjoc201304002 Previous Articles Next Articles

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超声辐射下一锅法制备O-芳磺酰基芳醛肟

陈保华^a,b, 李记太^a, 兰瑞家^a,c, 陈国锋^a

a 河北大学化学与环境科学学院河北省分析科学技术重点实验室保定 071002;
b 河北大学药学院河北省药物质量研究重点实验室保定 071002;
c 廊坊师范学院化学与材料科学学院廊坊 065000

收稿日期:2013-04-01 修回日期:2013-04-26 发布日期:2013-05-13
通讯作者: 李记太 E-mail:lijitai@hbu.cn
基金资助:
河北省自然科学基金(No. B2012201052)资助项目

One-Pot Synthesis of O-Arylsulfonyl Arylaldoximes under Ultrasound Irradiation

Chen Baohua^a,b, Li Jitai^a, Lan Ruijia^a,c, Chen Guofeng^a

a Key Laboratory of Analytical Science and Technology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002;
b Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding 071002;
c Faculty of Chemistry and Material Science, Langfang Teachers' College, Langfang 065000

Received:2013-04-01 Revised:2013-04-26 Published:2013-05-13
Supported by:
Project supported by the Natural Science Foundation of Hebei Province (No. B2012201052)

One-pot synthesis of O-arylsulfonyl arylaldoximes was carried out in 56%～94% yields via the condensation of arylaldoxime with aromatic sulfonyl chloride in the presence of sodium hydroxide at room temperature in dichloromethane under ultrasound irradiation. The advantages of this methodology are convenient operation, mild conditions, short reaction times, and high yields.

Key words: O-arylsulfonyl arylaldoxime, synthetic methods, one-pot synthesis, sonochemistry

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Chen Baohua, Li Jitai, Lan Ruijia, Chen Guofeng. One-Pot Synthesis of O-Arylsulfonyl Arylaldoximes under Ultrasound Irradiation[J]. Chin. J. Org. Chem., 2013, 33(9): 1965-1969.

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[1] Hutchison, G. I.; Prager, R. H.; Ward, A. D. Aust. J. Chem. 1980, 33, 2477.
[2] (a) Heldt, W. Z. J. Am. Chem. Soc. 1958, 80, 5880.
(b) Heldt, W. Z. J. Am. Chem. Soc. 1958, 80, 5972.
[3] (a) Costa, A.; Mestres, R.; Riego, J. M. Synth. Commun. 1982, 12, 1003.
(b) Hattori, K.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1982, 23, 3395.
[4] Hattori, K.; Matsumura, Y.; Miyazaki, T.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 7368.
[5] Hatch, M. J.; Cram, D. J. J. Am. Chem. Soc. 1953, 75, 38.
[6] (a) O’Brien, C. Chem. Rev. 1964, 64, 81.
(b) Hyatt, J. A. J. Org. Chem. 1981, 46, 3953.
(c) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 124, 7640.
[7] Al-Awadi, N. A.; Elnagdi, M. H.; Kaul, K.; Ilingovan, S.; El-Dusouqui, O. M. E. Tetrahedron 1998, 54, 4633.
[8] Al-Awadi, N. A.; Elnagdi, M. H.; Kaul, K.; Ilingovan, S.; El-Dusouqui, O. M. E. J. Phys. Org. Chem. 1999, 12, 654.
[9] Crawford, R. J.; Woo, C. Can. J. Chem. 1965, 43, 1534.
[10] Kitamura, M.; Chiba, S.; Narasaka, K. Bull. Chem. Soc. Jpn. 2003, 76, 1063.
[11] Hassner, A.; Patchornik, G.; Pradhan, T. K.; Kumareswaran, R. J. Org. Chem. 2007, 72, 658.
[12] Deng, G. S.; Mo, H. H.; Luo, J.; Tang, L. Chin. J. Org. Chem. 2012, 32, 2177 (in Chinese).
(邓桂胜, 莫宏华, 罗景, 汤力, 有机化学, 2012, 32, 2177.)
[13] (a) Luche, J. L. Synthetic Organic Sonochemistry, Plenum Press, New York, 1998.
(b) Mason, T. J.; Peters, D. Practical Sonochemistry. Power Ultrasound Uses and Applications, 2nd ed., Ellis Horwood, New York, 2002.
[14] (a) Li, J. T.; Wang, S. X.; Chen, G. F.; Li, T. S. Curr. Org. Synth. 2005, 2, 415.
(b) Ratoarinoro, N.; Wilhelm, A. M.; Berlan, J.; Delmas, H. Chem. Eng. J. 1992, 50, 27.
(c) Mehrabi, H. Ultrason. Sonochem. 2012, 19, 125.
(d) Fu, Z. Y.; Shao, H. W. Ultrason. Sonochem. 2011, 18, 520.
[15] (a) Li, J. T.; Zhai, X. L.; Chen, G. F. Ultrason. Sonochem. 2010, 17, 356.
(b) Li, J. T.; Yin, Y.; Sun, M. X. Ultrason. Sonochem. 2010, 17, 363.
[16] (a) Li, J. T.; Li, X. L. Ultrason. Sonochem. 2007, 14, 677.
(b) Li, J. T.; Li, X. L.; Liu, X. F.; Ma, J. J. Chin. J. Org. Chem. 2008, 28, 628 (in Chinese).
(李记太, 李晓亮, 刘献锋, 马洁洁, 有机化学, 2008, 28, 628.)
[17] (a) Louisnard, O. Ultrason. Sonochem. 2012, 19, 56.
(b) Louisnard, O. Ultrason. Sonochem. 2012, 19, 66.
[18] Li, J. T.; Li, X. L.; Li, T. S. Ultrason. Sonochem. 2006, 13, 200

超声辐射下一锅法制备O-芳磺酰基芳醛肟

One-Pot Synthesis of O-Arylsulfonyl Arylaldoximes under Ultrasound Irradiation

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