Synthesis and Optical Properties of Novel Spiro[chromo(2,3-c)-pyrazole-4,1'-isobenzofuran]-3'-one Compounds

doi:10.6023/cjoc201907033

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (2): 501-510.DOI: 10.6023/cjoc201907033 Previous Articles Next Articles

新型螺[色烯并(2,3-c)吡唑-4,1'-异苯并呋喃]-3'-酮类化合物的合成及光学性能研究

岳永双, 解正峰, 褚义成, 薛松松

西南石油大学化学化工学院油气田应用化学四川省重点实验室成都 615000

收稿日期:2019-07-24 修回日期:2019-09-09 发布日期:2019-10-09
通讯作者: 解正峰 E-mail:xiezhf@swpu.edu.cn
基金资助:
西南石油大学精细化学品青年科技创新团队（No.2017CXTD05）资助项目.

Synthesis and Optical Properties of Novel Spiro[chromo(2,3-c)-pyrazole-4,1'-isobenzofuran]-3'-one Compounds

Yue Yongshuang, Xie Zhengfeng, Chu Yicheng, Xue Songsong

Oil&Gas Field Applied Chemistry Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500

Received:2019-07-24 Revised:2019-09-09 Published:2019-10-09
Supported by:
Project supported by the Youth Science and Technology Innovation Team of Southwest Petroleum University (No. 2017CXTD05).

1. 200501S.pdf.pdf(1955KB)

Abstract

A series of novel spiro[chromo(2,3-c)pyrazole-4,1'-isobenzofuran]-3'-one compounds were synthesized via Knoevenagel condensation and dehydration reaction of 2-(4-dibutylamino-2-hydroxybenzoyl)benzoic acid or 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoic acid with pyrazolones using acid as catalysts and dehydrants. The effects of the ratio of the substrates, catalyst, temperature and reaction time were examined. Their optical properties in different pH and solvent were investigated. It shows that 1-(4-chlorophenyl)-7-(diethylamino)-3-methyl-1H,3'H-spiro[chromene[2,3-c]pyrazole-4,1'-isobenzofuran]-3'-one (1e) and 1-(4-chlorophenyl)-7-(dibutylamino)-3-methyl-1H,3'H-spiro[chromene[2,3-c]pyrazole-4,1'-isobenzofuran]-3'-one (1j) have potential as pH indicators for strong acids and bases.

Key words: spiro[chromo(2,3-c)pyrazole-4,1'-isobenzofuran]-3'-one, pyrazolone, Knoevenagel reaction, pH

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Yue Yongshuang, Xie Zhengfeng, Chu Yicheng, Xue Songsong. Synthesis and Optical Properties of Novel Spiro[chromo(2,3-c)-pyrazole-4,1'-isobenzofuran]-3'-one Compounds[J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 501-510.

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References

[1] Wan, D.; Li, Y.-X.; Zhu, P. Sens. Actuators, B 2015, 221, 1271.
[2] Liu, T.-Q.; Wan, X.-J.; Yao, Y.-W. Sens. Actuators, B 2017, 254, 1094.
[3] Hou, S.; Qu, Z.; Zhong, K.; Bian, Y.; Tang, L. Tetrahedron Lett. 2016, 57, 2616.
[4] Jiao, Y.; Zhang, L.; Zhou, P. Talanta 2016, 150, 14.
[5] Tao, Z.; Wu, B.; Zou, Z.; Wu, Y.; Zheng, J.; Wong, W.-K.; Wong, K. L. J. Lumin. 2016, 170, 187.
[6] Wang, S.; Li, C.; Li, J.; Chen, B.; Guo, Y. Acta Chim. Sinica 2017, 75, 383(in Chinese). (王少静, 李长伟, 李锦, 陈邦, 郭媛, 化学学报, 2017, 75, 383.)
[7] Ma, W.; Xia, W.; Xu, Q.; Han, H.; Song, B.; Sun, L.; Liang, C. Acta Chim. Sinica 2012, 70, 917(in Chinese). (马文辉, 夏威, 徐群, 韩宏彦, 宋波, 孙丽微, 梁春花, 化学学报, 2012, 70, 917.)
[8] Dujols, V.; Czarnik, A. W. J. Am. Chem. Soc. 1997, 119, 7386.
[9] Kim, H. N.; Lee, M. H.; Kim, H. J.; Kim, J. S.; Yoon, J. Chem. Soc. Rev. 2008, 37, 1465.
[10] Xiang, Y.; Tong, A.; Jin, P.; Ju, Y. Org. Lett. 2006, 8, 2863.
[11] Zheng, H.; Qian, Z.-H.; Xu, L.; Yuan, F.-F.; Lan, L.-D.; Xu, J.-G. Org. Lett. 2006, 8, 859.
[12] Yang, Y. K.; Cho, H. J.; Lee, J.; Shin, I.; Tae, J. Org. Lett. 2009, 11, 859.
[13] Cai, L.; Lü, L.; Wang, M.; Wu, Y.; Huang, J.; Zeng, X. Chin. J. Org. Chem. 2018, 38, 158(in Chinese). (蔡柳, 吕柳, 王梦颖, 吴禹胜, 黄锦锋, 曾向潮, 有机化学, 2018, 38, 158.)
[14] Hong, M.; Lu, S.; Feng, L.; Xu, D. Dyes Pigm. 2016, 127, 94.
[15] Hao, Y.; Xie, Z.; Bao, W.; Wang, X.; Shi, W. Chin. J. Org. Chem. 2018, 38, 2109(in Chinese). (郝云鹏, 解正峰, 包万睿, 王馨, 石伟, 有机化学, 2018, 38, 2109.)
[16] Yue, Y.; Xie, Z.; Chu, Y.; Shi, W. Russ. J. Org. Chem. 2019, 55, 866.
[17] Feng, L.; Shi, W.; Ma, J.; Chen, Y.; Fan, K.; Hui, Y.; Xie, Z. Sens. Actuators, B 2016, 237, 563
[18] Li, Y.; Shi, W.; Ma J.; Wang, X.; Kong, X.; Zhang, Y.; Feng, L.; Hui, Y.; Xie, Z. J. Photochem. Photobiol. A 2017, 338, 1
[19] Wang, X.; Shi, W.; Feng, L.; Ma, J.; Li Y.; Kong X.; Chen, Y.; Hui, Y.; Xie, Z. Inorg. Chem. Commun. 2017, 79, 50.
[20] Chu, Y.; Xie, Z.; Yue, Y.; Yue, Y.; Kong, X.; Shi, W.; Feng, S. ACS Omega 2019, 4, 5367.
[21] Kim, I. J.; Ramalingam, M.; Son, Y. A. Dyes Pigm. 2018, 151, 64.
[22] Wang, Y.; Lv, X.; Guo, W. Dyes Pigm. 2017, 139, 482.
[23] Liu, J.; Sun, Y.-Q.; Wang, P.; Zhang, J.; Guo, W. Analyst 2013, 138, 2654.
[24] Huang, K.; Liu, M.; Liu, Z.; Cao, D.; Jing, H.; Zeng, W. Dyes Pigm. 2015, 118, 88.
[25] Ge, J.; Fan, L.; Zhang, K.; Ou, T.; Li, Y.; Zhang, C.; Dong, C.; Shuang, S.; Wong, M. S. Sens. Actuators, B 2018, 262, 913.
[26] Zhang, X.; Jing, S.-Y.; Huang, S.-Y.; Zhou, X.-W.; Bai, J.-M.; Zhao, B.-X. Sens. Actuators, B 2015, 206, 663.

新型螺[色烯并(2,3-c)吡唑-4,1'-异苯并呋喃]-3'-酮类化合物的合成及光学性能研究

Synthesis and Optical Properties of Novel Spiro[chromo(2,3-c)-pyrazole-4,1'-isobenzofuran]-3'-one Compounds

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