Three-Component Synthesis of Chromeno[4,3-d]pyrazolo[3,4-b]-pyridine Derivatives and Their Fluorescence Properties

doi:10.6023/cjoc201809042

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (4): 1085-1094.DOI: 10.6023/cjoc201809042 Previous Articles Next Articles

Articles

色烯并[4,3-d]吡唑并[3,4-b]吡啶衍生物的三组分合成及荧光性质研究

张梦烨, 王宁, 徐文韬, 黄志斌, 史达清

苏州大学材料与化学化工学部江苏省有机合成重点实验室苏州 215123

收稿日期:2018-09-29 修回日期:2018-12-10 发布日期:2018-12-21
通讯作者: 黄志斌, 史达清 E-mail:dqshi@suda.edu.cn;zbhuang@suda.edu.cn
基金资助:
江苏省高校自然科学重大研究（Nos.15KJA150006，17KJA150006）资助项目.

Three-Component Synthesis of Chromeno[4,3-d]pyrazolo[3,4-b]-pyridine Derivatives and Their Fluorescence Properties

Zhang Mengye, Wang Ning, Xu Wentao, Huang Zhibin, Shi Daqing

College of Chemistry, Chemical Engineering and Materials Science, Key Laboratory of Organic Synthesis of Jiangsu Province, Soochow University, Suzhou 215123

Received:2018-09-29 Revised:2018-12-10 Published:2018-12-21
Contact: 10.6023/cjoc201809042 E-mail:dqshi@suda.edu.cn;zbhuang@suda.edu.cn
Supported by:
Project supported by the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (Nos.15KJA150006,17KJA150006).

1. Three-Component Synthesis of Chromeno[4,3-d]pyrazolo[3,4-b]-pyridine Derivatives and Their Fluorescence Properties.PDF(2965KB)

Abstract

A series of 5-aminochromeno[4,3-d]pyrazolo[3,4-b]pyridin-6(3H)-one derivatives 4a~4w were synthesized by three-component reactions of salicylaldehydes, ethyl cyanoacetate and 5-aminopyrazoles catalyzed by triethylamine (TEA). The properties of the synthesized compounds were examined by fluorescence spectroscopy and the results indicated that some compounds were possessed high fluorescence quantum yields.

Key words: chromeno[4,3-d]pyrazolo[3,4-b]pyridine, three-component synthesis, fluorescence property

Cite this article

Zhang Mengye, Wang Ning, Xu Wentao, Huang Zhibin, Shi Daqing. Three-Component Synthesis of Chromeno[4,3-d]pyrazolo[3,4-b]-pyridine Derivatives and Their Fluorescence Properties[J]. Chin. J. Org. Chem., 2019, 39(4): 1085-1094.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Shi, Y.; Zhou, C. H. Bioorg. Med. Chem. Lett. 2011, 21, 956.
(b) Laxmi, S. V.; Kuarm, B. S.; Rajitha, B. Med. Chem. Res. 2013, 22, 768.
(c) Varun, G.; Bhila, C. V.; Patel, N. H.; Patel, D. I. B. Med. Chem. Res. 2013, 22, 4338.
[2] Hemshekhar, M.; Sunitha, K.; Thushara, R. M.; Santhosh, S.; Sundaram, M. S.; Kemparaju, K.; Girish, K. S. Biochimie 2013, 95, 1326.
[3] (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.; Oliveira-Campos, A. M.; Rodrigues, L. M. Eur. J. Med. Chem. 2012, 47, 370.
(c) Li, B.; Liu, Q. X.; Zhou, Y. Q.; Jia, Z. D.; Zhu, M. Y.; Xu, Y.; Song, M. P. Chin. J. Org. Chem. 2017, 37, 2008(in Chinese).(李标, 刘秋霞, 周元清, 贾赵栋, 朱曼毓, 徐琰, 宋毛平, 有机化学, 2017, 37, 2008.)
(d) Huang, X. W.; Liu, J. L. Chin. J. Org. Chem. 2018, 38, 1233(in Chinese).(黄新炜, 刘建利, 有机化学, 2018, 38, 1233.)
[4] Daly, A. K. Arch. Toxicol. 2013, 87, 407.
[5] (a) Kirkiacharian, S.; Thuy, D. T.; Sicsic, S. Farmaco 2002, 57, 703.
(b) Kashman, Y. J. Med. Chem. 1992, 35, 2735.
[6] (a) Lin, Q. H.; Bao, C. Y.; Cheng, S. Y.; Yang, Y. L.; Ji, W.; Zhu, L. Y. J. Am. Chem. Soc. 2012, 134, 5052.
(b) Hirano, T.; Kubo, H.; Shiraishi, T.; Hiromoto, K.; Fujiwara, T.; Kagechika, H. Tetrahedron Lett. 2012, 53, 5916.
(c) Sanap, K. K.; Samant, S. D. Tetrahedron Lett. 2012, 53, 5407.
[7] (a) Zhao, Y. R.; Zheng, Q.; Dakin, K.; Xu, K.; Martinez, M. L.; Li, W. H. J. Am. Chem. Soc. 2004, 126, 4653.
(b) Lee, K. S.; Kim, H. J.; Kim, G. H.; Shin, I.; Hong, J. I. Org. Lett. 2008, 10, 49.
(c) Huang, Q.; Qu, W. J.; Chen, J.; Lin, Q.; Yao, H.; Zhang, Y. M.; Wei, T. B. Chin. J. Org. Chem. 2018, 38, 629(in Chinese).(黄青, 曲文娟, 陈洁, 林奇, 姚虹, 张有明, 魏太保, 有机化学, 2018, 38, 629.)
[8] 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.
[9] (a) Liu, X. C.; Lin, W.; Wang, H. Y.; Huang, Z. B.; Shi, D. Q. J. Heterocycl. Chem. 2014, 51, 1036.
(b) 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.)
[10] (a) You, X. W.; Yu, H.; Wang, M. G.; Wu, J.; Shang, Z. C. Lett. Org. Chem. 2012, 9, 19.
(b) Jin, P. P.; Liu, X. C.; Liu, D. Q.; Huang, Z. B.; Shi, D. Q. J. Heterocycl. Chem. 2015, 52, 1625.
(c) Lin, W.; Cai, Q.; Zheng, C. Z.; Zheng, Y. X.; Shi, D. Q. Chin. J. Org. Chem. 2017, 37, 2392(in Chinese).(林伟, 蔡琦, 郑纯智, 郑永祥, 史达清, 有机化学, 2017, 37, 2392.)
[11] (a) Posner, G. H. Chem. Rev. 1986, 86, 831.
(b) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123.
(c) Wan, J. P.; Gan, L.; Liu, Y. Org. Biomol. Chem. 2017, 15, 9031.
(d) Wan, J. P.; Liu, Y. RSC Adv. 2012, 2, 9763.
[12] (a) Sarkar, S.; Khan, A. T. Chem. Commun. 2015, 51, 12673.
(b) Guo, W. S.; Xin, X.; Zhao, K. L.; Wen, L. R.; Li, M. RSC Adv. 2015, 5, 70429.
(c) Jiang, B.; Fan, W.; Sun, M. Y.; Ye, Q.; Wang, S. L.; Tu, S. J.; Li, G. J. Org. Chem. 2014, 79, 5258.
(d) Shi, G. H.; He, X. W.; Shang, Y. J.; Xiang, L. W.; Yang, C.; Han, G.; Du, B. Chin. J. Chem. 2016, 34, 901.
(e) Xiao, M.; Yan, C. G. Chin. J. Chem. 2017, 35, 1422.
(f) Gao, G.; Wang, P.; Liu, P.; Zhag, W. H.; Mo, L. P.; Zhang, Z. H. Chin. J. Org. Chem. 2018, 38, 846(in Chinese).(高歌, 王萍, 刘鹏, 张卫红, 默丽萍, 张占辉, 有机化学, 2018, 38, 846.)
(g) Wan, J. P.; Lin, Y.; Huang, Q.; Liu, Y. J. Org. Chem. 2014, 79, 7232.
(h) Wan, J. P.; Gao, S.; Liu, Y. J. Org. Chem. 2015, 80, 9028.
(i) Wan, J. P.; Lin, Y.; Jing, Y.; Xu, M.; Liu, Y. Tetrahedron 2014, 70, 7874.
[13] (a) Feng, X.; Wang, J. J.; Xun, Z.; Zhang, J. J.; Huang, Z. B.; Shi, D. Q. Chem. Commun. 2015, 51, 1528.
(b) Feng, X.; Wang, J. J.; Xun, Z.; Huang, Z. B.; Shi, D. Q. J. Org. Chem. 2015, 80, 1025.
(c) Wang, J. J.; Feng, X.; Xun, Z.; Shi, D. Q.; Huang, Z. B. J. Org. Chem. 2015, 80, 8435.
(d) Xun, Z.; Feng, X.; Wang, J. J.; Shi, D. Q.; Huang, Z. B. Chin. J. Chem. 2016, 34, 696.

色烯并[4,3-d]吡唑并[3,4-b]吡啶衍生物的三组分合成及荧光性质研究

Three-Component Synthesis of Chromeno[4,3-d]pyrazolo[3,4-b]-pyridine Derivatives and Their Fluorescence Properties

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 9

Recommended Articles

Metrics

Comments

[1]	Gaige Zhu, Xiaohui Lai, Siyu Wang, Caixia Lin, Yaofeng Yuan. Synthesis of 2-Imino-1,2-dihydroquinolines via Copper Catalysis [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2810-2819.
[2]	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.
[3]	Wang Hui, Zhang Yonghong, Tao Jingqi, Zeng Zhuo, Zeng Heping. Synthesis and Photoluminescence Properties of 8-Hydroxyquinoline Schiff Base Derivatives and Their Metal Complexes [J]. Chin. J. Org. Chem., 2012, 32(02): 354-359 .
[4]	FAN Mei, XIE Zhi-Xiong, XU Zhi-Han, PING Bing, ZHAO Sheng-Yin. Synthesis and Fluorescence Properties of N-Benzamidobisindolylmaleimide Derivatives [J]. Chin. J. Org. Chem., 2011, 31(06): 843-849.
[5]	LI Gang, GONG Wei-Tao, YE Jun-Wei, LIN Yuan, NING Gui-Ling. Synthesis of α-Monosubstituted Pyridinium Salts and Their Photochemical Reaction [J]. Chin. J. Org. Chem., 2011, 31(02): 216-221.
[6]	WANG Shun, GU Yong-Gong. Synthesis, Structure Characterization of New Derivatives of Porphyrin and Study on Their Electrochemical Properties [J]. Chin. J. Org. Chem., 2009, 29(11): 1762-1767.
[7]	Meng, Kang; Qian, Ying*. Synthesis and Fluorescence Properties of Bisbranched 1,3,4-Oxadiazole Derivatives [J]. Chin. J. Org. Chem., 2009, 29(01): 71-77.
[8]	FANG Qing,ZENG He-Ping*,ZHANG Wei-Min,ZHANG Pei-Quan. Synthesis and Fluorescence of Bis{2-{2-{9-ethyl-6-[2-(8-hydroxy-quinolin-2-yl)vinyl]carbazol-3-yl}vinyl}-8-quinolinolato} Zn Complex [J]. Chin. J. Org. Chem., 2008, 28(05): 814-818.
[9]	OUYANG Xin-Hua,ZENG He-Ping*,XIE Yan. Synthesis and Photoluminescence Properties of 8-Hydroxyquinoline Derivatives and Their Metalion Complexes [J]. Chin. J. Org. Chem., 2007, 27(03): 402-408.