One-Pot Synthesis of 4-Thiazolidinone Derivatives Catalyzed by Zinc Acetate-Schiff Base Complex Immobilized on Mesoporous Molecular Sieve MCM-41

doi:10.6023/cjoc201601014

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (8): 1942-1947.DOI: 10.6023/cjoc201601014 Previous Articles Next Articles

NOTE

介孔分子筛MCM-41固载席夫碱与醋酸锌共催化“一锅法”合成噻唑啉酮衍生物

邢雪建^a, 樊馗^a, 庞海霞^a, 吴阳^a, 杨敬辉^a, 石伟^a,b, 解正峰^a,b, 惠永海^a

a 新疆大学化学化工学院石油天然气精细化工教育部重点实验室乌鲁木齐 830046;
b 西南石油大学化学化工学院成都 610500

收稿日期:2016-01-14 修回日期:2016-04-02 发布日期:2016-04-15
通讯作者: 惠永海 E-mail:hyhai97@126.com
基金资助:
国家自然科学基金（Nos. 21161026，21362036）和新疆自治区研究生科研创新（No. XJGRI2015013）资助项目.

One-Pot Synthesis of 4-Thiazolidinone Derivatives Catalyzed by Zinc Acetate-Schiff Base Complex Immobilized on Mesoporous Molecular Sieve MCM-41

Xing Xuejian^a, Fan Kui^a, Pang Haixia^a, Wu Yang^a, Yang Jinghui^a, Shi Wei^a,b, Xie Zhengfeng^a,b, Hui Yonghai^a

a Key Laboratory of Oil & Gas Fine Chemicals, Ministry of Education & Xinjiang Uyghur Autonomous Region, College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046;
b School of Chemistry and Chemistry Engineering, Southwest Petroleum University, Chengdu 610500

Received:2016-01-14 Revised:2016-04-02 Published:2016-04-15
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21161026, 21362036) and the Postgraduate Innovative Foundation of Xinjiang Autonomous Region (No. XJGRI2015013).

1. One-Pot Synthesis of 4-Thiazolidinone Derivatives Catalyzed by Zinc Acetate-Schiff Base Complex Immobilized on Mesoporous Molecular Sieve MCM-41.PDF(2443KB)

Abstract

A new simple and efficient one-pot synthesis of thiazolidinone derivatives via aldehydes, amines and mercaptoacetic acid in the presence of Zn(OAc)₂-Schiff base complex immobilized on MCM-41 is described. A variety of aldehydes and amines were engaged in the study and afforded respective thiazolidinones in high yield (up to 98%). Moreover, consistent activity of recovered catalyst was found to be almost same up to five cycles in 80% yield.

Key words: mesoporous molecular sieve MCM-41, Schiff base, one-pot synthesis, thiazolidinone, catalysis

Cite this article

Xing Xuejian, Fan Kui, Pang Haixia, Wu Yang, Yang Jinghui, Shi Wei, Xie Zhengfeng, Hui Yonghai. One-Pot Synthesis of 4-Thiazolidinone Derivatives Catalyzed by Zinc Acetate-Schiff Base Complex Immobilized on Mesoporous Molecular Sieve MCM-41[J]. Chin. J. Org. Chem., 2016, 36(8): 1942-1947.

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[1] Perez, C.; Monserrat, J. P. Chen, Y.; Cohen, S. M. Chem. Commun. 2015, 51, 7116.
[2] Palekar, V. S.; Damle, A. J.; Shukla, S. R. Eur. J. Med. Chem. 2009, 44, 5112.
[3] Hosamani, K. M.; Shingalapur, R. V. Arch. Pharm. 2011, 344, 311.
[4] Li, Y. J.; Li, C. Y.; Jin, K.; Sun, S. Q.; Zhou, X. X. Acta Chim. Sinica 2012, 70, 151 (in Chinese).
(李英俊, 李春燕, 靳焜, 孙淑琴, 周晓霞, 化学学报, 2012, 70, 151.)
[5] Kitano, M.; Yagisawa, M.; Morimoto, Y. EP 387028, 1990 [Chem. Abstr. 1991, 114, 101981].
[6] Srivastava, T.; Haq, W.; Katti, S. B. Tetrahedron 2002, 58, 7619.
[7] Rawal, R. K.; Srivastava, T.; Haq, W.; Katti, S. B. J. Chem. Res. 2004, 5, 368.
[8] Sharma, R. C.; Kumar, D. J. Indian Chem. Soc. 2000, 77, 492.
[9] Thakare, M. P.; Kumar, P.; Kumar, N.; Pandey, S. K. Tetrahedron Lett. 2014, 55, 2463.
[10] Dong, X. Z.; Hui, Y. H.; Xie, S. L.; Zhang, P.; Zhou, G. P.; Xie, Z. F. RSC Adv. 2013, 3, 3222.
[11] Xie, S. L.; Hui, Y. H.; Long, X. J.; Wang, C. C.; Xie, Z. F. Chin. Chem. Lett. 2013, 24, 28.
[12] Wang, C. C.; Xie, S. L.; Xie, Z. F.; Hui, Y. H. Chin. J. Org. Chem. 2013, 33, 2391 (in Chinese).
(王长春, 谢绍雷, 解正峰, 惠永海, 有机化学, 2013, 33, 2391.)
[13] Fan, K.; Hui, Y. H.; Hu, X. M.; Shi, W.; Pang, H. X.; Xie, Z. F. New J. Chem. 2015, 39, 5916.
[14] Zhou, G. P.; Yu, L.; Hui, Y. H.; Xie, Z. F. Acta Chim. Sinica 2012, 70, 1289 (in Chinese).
(周广鹏, 余蕾, 惠永海, 解正峰, 化学学报, 2012, 70, 1289.)
[15] Fu, Y. H.; Shi, H. L.; Zhou, G. P.; Hui, Y. H.; Xie, Z. F. Chin. J. Appl. Chem. 2015, 32, 1259 (in Chinese).
(付亚红, 师红丽, 周广鹏, 惠永海, 解正峰, 应用化学, 2015, 32, 1259.)
[16] Zhu, G. M.; Yang, L. M.; Cui, D. M. Chin. J. Org. Chem. 2014, 34, 495 (in Chinese).
(朱观明, 杨柳明, 崔冬梅, 有机化学, 2014, 34, 495.)
[17] Kumar, D.; Sonawane, M.; Pujala, B.; Jain, V. K.; Bhagat, S.; Chakraborti, A. K. Green Chem. 2013, 15, 2872.
[18] Naser, F.; Sattar, E. Chin. Chem. Lett. 2013, 24, 389.
[19] Pacha, W.; Erlenmeyer, H. Helv. Chim. Acta 1956, 39, 1156.
[20] Pang, H. X.; Hui, Y. H.; Fan, K.; Xing, X. J.; Wu, Y.; Yang, J. H.; Shi, W.; Xie, Z. F. Chin. Chem. Lett. 2016, 27, 335.

介孔分子筛MCM-41固载席夫碱与醋酸锌共催化“一锅法”合成噻唑啉酮衍生物

One-Pot Synthesis of 4-Thiazolidinone Derivatives Catalyzed by Zinc Acetate-Schiff Base Complex Immobilized on Mesoporous Molecular Sieve MCM-41

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