Synthesis of Functionalized Coumarino[4,3-d]pyrazolo[3,4-b]pyridine Derivatives and Their Selective Recognition for Zn2+

doi:10.6023/cjoc201702032

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (9): 2392-2398.DOI: 10.6023/cjoc201702032 Previous Articles Next Articles

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官能团化香豆素并[4,3-d]吡唑并[3,4-b]吡啶衍生物的合成及其对锌离子的选择性识别

林伟^a, 蔡琦^a, 郑纯智^a, 郑永祥^b, 史达清^b

a 江苏理工学院化学与环境工程学院常州 213001;
b 苏州大学材料与化学化工学部苏州 215123

收稿日期:2017-02-23 修回日期:2017-04-17 发布日期:2017-05-02
通讯作者: 林伟, 史达清 E-mail:linwei@jsut.edu.cn;dqshi@suda.edu.cn
基金资助:
国家自然科学基金（No.21502074）和江苏省高校自然科学重大研究（No.15KJA150006）资助项目.

Synthesis of Functionalized Coumarino[4,3-d]pyrazolo[3,4-b]pyridine Derivatives and Their Selective Recognition for Zn²⁺

Lin Wei^a, Cai Qi^a, Zheng Chunzhi^a, Zheng Yongxiang^b, Shi Daqing^b

a School of Chemistry and Environmental Engineering, Jiangsu University of Technology, Changzhou 213001;
b College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123

Received:2017-02-23 Revised:2017-04-17 Published:2017-05-02
Contact: 10.6023/cjoc201702032 E-mail:linwei@jsut.edu.cn;dqshi@suda.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21502074) and the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (No. 15KJA150006).

1. Synthesis of Functionalized Coumarino[4,3-d]pyrazolo[3,4-b]pyridine Derivatives and Their Selective Recognition for Zn²⁺.PDF(471KB)

Abstract

A series of functionalized coumarino[4,3-d]pyrazolo[3,4-b]pyridine derivatives 3a~3h were synthesized by the addition and cyclization of 3-acetoacetylcoumarin with 5-aminopyrazole catalyzed by CuSO₄. Some of the synthesized compounds had high fluorescence quantum yields. The properties of the compounds with cations such as Ag⁺, Cr³⁺, Co²⁺, Cu²⁺, Pb²⁺, Sn⁴⁺, Fe³⁺ and Zn²⁺ were examined by fluorescence spectroscopy. The results showed that compounds 3a and 3b have selective recognition for Zn²⁺.

Key words: coumarino[4,3-d]pyrazolo[3,4-b]pyridine derivative, synthesis, fluorescence property, Zn²⁺, selective recognition

Cite this article

Lin Wei, Cai Qi, Zheng Chunzhi, Zheng Yongxiang, Shi Daqing. Synthesis of Functionalized Coumarino[4,3-d]pyrazolo[3,4-b]pyridine Derivatives and Their Selective Recognition for Zn²⁺[J]. Chin. J. Org. Chem., 2017, 37(9): 2392-2398.

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[1] (a) Shi, Y.; Zhou, C. H. Bioorg. Med. Chem. Lett. 2011, 21, 956.
(b) Varun, G.; Bhila, C. V.; Patel, N. H.; Patel, D. I. B. Med. Chem. Res. 2013, 22, 4338.
(c) Laxmi, S. V.; Kuarm, B. S.; Rajitha, B. Med. Chem. Res. 2013, 22, 768.
[2] Hemshekhar, M.; Sunitha, K.; Thushara, R. M.; Santhosh, S.; Sundaram, M. S.; Kemparaju, K.; Girish, K. S. Biochimie 2013, 95, 1326.
[3] (a) Kirkiacharian, S.; Thuy, D. T.; Sicsic, S. Farmaco 2002, 57, 703.
(b) Kashman, Y. J. Med. Chem. 1992, 35, 2735.
[4] (a) Li, W.; Sun, Y. N.; Yan, X. T.; Yang, S. Y.; Kim, E. J.; Kang, H. K.; Kim, Y. H. J. Agric. Food Chem. 2013, 61, 10730.
(b) Francisco, C. S.; Rodrigues, L. R.; Cerqueira, N. M.; OliveiraCampos, A. M.; Rodrigues, L. M. Eur. J. Med. Chem. 2012, 47, 370.
[5] Daly, A. K. Arch. Toxicol. 2013, 87, 407.
[6] (a) Sanap, K. K.; Samant, S. D. Tetrahedron Lett. 2012, 53, 5407.
(b) Hirano, T.; Kubo, H.; Shiraishi, T.; Hiromoto, K.; Fujiwara, T.; Kagechika, H. Tetrahedron Lett. 2012, 53, 5916.
(c) Lin, Q. H.; Bao, C. Y.; Cheng, S. Y.; Yang, Y. L.; Ji, W.; Zhu, L. Y. J. Am. Chem. Soc. 2012, 134, 5052.
(d) Li, Q.; Zeng, Y.; Zhang, X. H.; Yu, T. J.; Chen, J. P.; Li, Y. Acta Chim. Sinica 2015, 73, 826(in Chinese). (李婧, 曾毅, 张小辉, 于天君, 陈金平, 李嫕, 化学学报, 2015,73, 826.)
[7] (a) Ast, S.; Muller, H.; Flehr, R.; Klamroth, T.; Walz, B.; Holdt, H. J. Chem. Commun. 2011, 47, 4685.
(b) Dong, Y.; Li, J. F.; Jiang, X. X.; Song, F. Y.; Cheng, Y. X.; Zhu, C. J. Org. Lett. 2011, 13, 2252.
(c) Yan, L. Q.; Xie, M. S.; Peng, M. S.; Liu, W. Aust. J. Chem. 2013, 66, 1584.
(d) Wang, L. Y.; Li, H. H.; Cao, D. R. Sens. Actuators B, Chem. 2013, 181, 749.
(e) Li, C. W.; Yang, D.; Yi, B.; Guo, Y. Chin. J. Org. Chem. 2016, 36, 787(in Chinese). (李长伟, 杨栋, 尹兵, 郭媛, 有机化学, 2016, 36, 787.)
[8] (a) Kang, C.; Kim, J. S. Org. Lett. 2011, 13, 5056.
(b) Li, G. P.; Zhu, D. J.; Liu, Q.; Xue, L.; Jiang, H. Org. Lett. 2013, 15, 2002.
(c) Yan, X. Q.; Zhuo, J. B.; Wang, J. C.; Xie, L. L.; Yuan, Y. F. Chin. J. Org. Chem. 2015, 35, 2184(in Chinese). (晏希泉, 卓继斌, 王吉成, 谢莉莉, 袁耀锋, 有机化学, 2015, 35, 2184.)
[9] Yang, Y. T.; Huo, F. J.; Yin, C. X.; Zhang, A. M.; Chao, J. B.; Li, Y. Q.; Nie, Z. X.; Ramon, M. M.; Liu, D. S. Biosens. Bioelectron. 2013, 47, 300.
[10] Li, K. T.; Lin, Y. B.; Yang, D. Y. Org. Lett. 2012, 14, 1190.
[11] Lin, C. H.; Yang, D. Y. Org. Lett. 2013, 15, 2802.
[12] Chen, J. H.; Liu, W. M.; Ma, J. J.; Xu, H. T.; Wu, J. S.; Tang, X. L.; Fan, Z. Y.; Wang, P. F. J. Org. Chem. 2012, 77, 3475.
[13] Atsushi, T. Brain Res. Rev. 2000, 34, 137.
[14] Robert, A. C.; William, R. H.; Charles, P. F.; Wolfqang, M. Metallomics 2010, 2, 306.
[15] (a) De Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
(b) Mikata, Y.; Wakamatsu, M.; Yano, S. Dalton Trans. 2005, 5, 545.
(c) Mikata, Y.; Wakamatsu, M.; Kawamura, A.; Yamanaka, N.; Yano, S.; Odani, A.; Morihiro, K.; Tamotsu, S. Inorg. Chem. 2006, 45, 9262.
[16] (a) Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. J. Am. Chem. Soc. 2000, 122, 12399.
(b) Gee, K. R.; Zhou, Z. L.; Qian, W. J.; Kennedy, R. J. Am. Chem. Soc. 2002, 124, 776.
(c) Gou, M.; Tong, L. B.; Jiang, L.; Sun, J.; Yin, G. Chin. J. Inorg. Chem. 2009, 25, 956(in Chinese). (郭敏, 佟履冰, 姜李, 孙剑, 尹桂, 无机化学学报, 2009, 25, 956.)
[17] (a) Tang, B.; Wang, X. Q.; Zhang, Z. D. Chin. J. Appl. Chem. 1997, 14, 28(in Chinese). (唐波, 王晓清, 张志德, 应用化学, 1997, 14, 28.)
(b) Wu, L. H.; Xue, W. X. Chem. World 2009, 50, 529(in Chinese). (吴粦华, 薛王欣, 化学世界, 2009, 50, 529.)
[18] Han, H. M.; Wu, Y. G.; Xiao, S. J. Chin. J. Inorg. Chem. 2010, 26, 1426(in Chinese). (韩换美, 吴亚光, 肖守军, 无机化学学报, 2010, 26, 1426.)
[19] Shen, P.; Hu, S. L. Chem. Reagents 2012, 34, 737(in Chinese). (沈萍, 胡胜利, 化学试剂, 2012, 34, 737.)
[20] (a) Wang, H. Y.; Liu, X. C.; Feng, X.; Huang, Z. B.; Shi, D. Q. Green Chem. 2013, 15, 3307.
(b) Wang, H. Y.; Liu, X. C.; Huang, Z. B.; Shi, D. Q. J. Heterocycl. Chem. 2015, 52, 380.
(c) Liu, X. C.; Lin, W.; Feng, X.; Huang, Z. B.; Shi, D. Q. J. Heterocycl. Chem. 2014, 51, 1036.
(d) Jin, P. P.; Liu, X. C.; Liu, D. Q.; Huang, Z. B.; Shi, D. Q. J. Heterocycl. Chem. 2015, 52, 1625.
(e) Wang, J. X.; Lin, W.; Liu, H. T.; Hu, M. H.; Feng, X.; Ren, J. F.; Huang, Z. B.; Shi, D. Q. Chin. J. Org. Chem. 2015, 35, 927(in Chinese). (王菊仙, 林伟, 刘洪涛, 胡明华, 冯贤, 任金凤, 黄志斌, 史达清, 有机化学, 2015, 35, 927.)
[21] Shi, C. L.; Shi, D. Q. J. Chem. Res. 2011, 585.

官能团化香豆素并[4,3-d]吡唑并[3,4-b]吡啶衍生物的合成及其对锌离子的选择性识别

Synthesis of Functionalized Coumarino[4,3-d]pyrazolo[3,4-b]pyridine Derivatives and Their Selective Recognition for Zn²⁺

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