Citation: Wang Bin, Ye Wenbo, Yan Zicong, Wan Changfeng, Hou Haoqing, Wang Zhiyong. A New Catalyst-Free Synthesis of 2, 3-Dicarboxylic Ester Quinoline Derivatives[J]. Chinese Journal of Organic Chemistry, ;2018, 38(2): 504-508. doi: 10.6023/cjoc201708054 shu

A New Catalyst-Free Synthesis of 2, 3-Dicarboxylic Ester Quinoline Derivatives

a.
College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022
b.
Department of Chemistry, University of Science and Technology of China, Hefei 230026

Corresponding author: Wan Changfeng, wanfeng@jxnu.edu.cn
Received Date: 25 August 2017
Revised Date: 11 October 2017
Available Online: 24 February 2017
Fund Project: the National Natural Science Foundation of China 21574060the National Natural Science Foundation of China 21402068the National Natural Science Foundation of China 21472177Project supported by the National Natural Science Foundation of China (Nos. 21402068, 21574060, 21472177)

Figures(2)

A high efficient method for the synthesis of 2, 3-dicarboxylic ester quinoline derivatives which employed o-amino diphenyl methylone derivatives and acetylenedicarboxylic esters as the reaction substrates was developed. This method possessed the character of catalyst-free and mild reaction conditions. Proposed mechanism was also studied according to the reaction result.
- quinoline derivatives,
- catalyst-free,
- green synthesis
1. [1]
  Chen, Y. L.; Chen, I. L.; Lu, C. M.; Tzeng, C. C.; Tsao, L. T.; Wang, J. P. Bioorg. Med. Chem. 2004, 12, 387. doi: 10.1016/j.bmc.2003.10.051
2. [2]
  Nayyar, A.; Malde, A.; Jain, R.; Coutinho, E. Bioorg. Med. Chem. 2006, 14, 7302.
3. [3]
  Narender, P.; Srinivas, U.; Ravinder, M.; Rao, B. A.; Ramesh, C.; Harakishore, K.; Gangadasu, B.; Murthy, U. S. N.; Rao, V. J. Bioorg. Med. Chem. 2006, 14, 4600. doi: 10.1016/j.bmc.2006.02.020
4. [4]
  Baba, A.; Kawamura, N.; Makino, H.; Ohta, Y.; Taketomi, S.; Sohda, T. J. Med. Chem. 1996, 39, 5176. doi: 10.1021/jm9509408
5. [5]
  Muruganantham, N.; Sivakumar, R.; Anbalagan, N.; Gunasekaran, V.; Leonard, J. T. Biol. Pharm. Bull. 2004, 27, 1683. doi: 10.1248/bpb.27.1683
6. [6]
  Nayyar, A.; Malde, A.; Coutinho, E.; Jain, R. Bioorg. Med. Chem. 2006, 14, 7302. doi: 10.1016/j.bmc.2006.06.049
7. [7]
8. [8]
9. [9]
  (a) Manske, R. H. F. ; Kulka, M. Org. React. 1953, 7, 59.
  (b) Ranu, B. C. ; Hajra, A. ; Dey, S. S. ; Jana, U. Tetrahedron 2003, 59, 813.
10. [10]
  Combes, A. Bull. Soc. Chim. Fr. 1888, 49, 89.
11. [11]
  (a) Friedlander, P. Chem. Ber. 1882, 15, 2572.
  (b) Marco-Contelles, J. ; Perez-Mayoral, E. ; Samadi, A. ; Carreiras, M. D. C. ; Soriano, E. Chem. Rev. 2009, 109, 2652.
12. [12]
  Chanda, T.; Verma, R. K.; Singh, M. S. Chem. -Asian J. 2012, 7, 778. doi: 10.1002/asia.v7.4
13. [13]
14. [14]
  Venkanna, A.; Swapn, K.; Rao, P. V. RSC Adv. 2014, 4, 15154. doi: 10.1039/c3ra47212d
15. [15]
  (a) Patil, D. R. ; Salunkhe, S. M. ; Deshmukh, M. B. ; Anbhule, P. V. J. Heterocycl. Chem. 2011, 48, 1414.
  (b) Zhou, W. ; Le, J. H. Chem. Commun. 2014, 50, 5583.
  (c) Asghari, S. ; Qandalee, M. ; Naderi, Z. ; Sobhaninia, Z. Mol. Diversity 2010, 14, 569.
  (d) Madhav, B. ; Murthy, S. N. ; Rao, K. R. ; Nageswar, Y. V. D. Helv. Chim. Acta 2010, 93, 257.
  (e) Patil, D. R. ; Deshmukh, M. B. ; Salunkhe, S. M. ; Anbhule, P. V. J. Heterocycl. Chem. 2011, 48, 1342.
16. [16]
  (a) Basle, O. ; Li, C. J. Green Chem. 2007, 9, 1047.
  (b) Li, C. J. Green Chem. 2002, 4, 1.
  (c) Hudson, R. ; Li, C. J. ; Moores, A. Green Chem. 2012, 14, 622.
17. [17]
  (a) Zhang, X. ; Wang, L. Green Chem. 2012, 14, 2141.
  (b) Zhang, X. ; Wang, M. ; Li, P. ; Wang, L. Chem. Commun. 2014, 50, 8006.
  (c) Zhao, Q. ; Li, H. ; Wang, L. Org. Biomol. Chem. 2013, 11, 6772.
18. [18]
  (a) Yang, Y. ; Bao, Y. J. ; Guan, Q. Q. ; Sun, Q. ; Zha, Z. G. ; Wang, Z. Y. Green Chem. 2017, 19, 112.
  (b) Yang, Y. ; Zhang, S. ; Tang, L. ; Hu, Y. B. ; Zha, Z. G. ; Wang, Z. Y. Green Chem. 2016, 18, 2609.
  (c) Tang, L. ; Guo, X. F. ; Yang, Y. ; Zha, Z. G. ; Wang, Z. Y. Chem. Commun. 2014, 6145.
1. [1]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
2. [2]
  Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
3. [3]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
4. [4]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
5. [5]
  Renxiu Zhang , Xin Zhao , Yunfei Zhang . Application of Electrochemical Synthesis in the Teaching of Organic Chemistry. University Chemistry, 2025, 40(4): 174-180. doi: 10.12461/PKU.DXHX202406116
6. [6]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
7. [7]
  Jia-He Li , Yu-Ze Liu , Jia-Hui Ma , Qing-Xiao Tong , Jian-Ji Zhong , Jing-Xin Jian . 洛芬碱衍生物的合成、化学发光与重金属离子检测. University Chemistry, 2025, 40(6): 230-237. doi: 10.12461/PKU.DXHX202407080
8. [8]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
9. [9]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
10. [10]
  Dan Li , Hui Xin , Xiaofeng Yi . Comprehensive Experimental Design on Ni-based Catalyst for Biofuel Production. University Chemistry, 2024, 39(8): 204-211. doi: 10.3866/PKU.DXHX202312046
11. [11]
  Wen YANG , Didi WANG , Ziyi HUANG , Yaping ZHOU , Yanyan FENG . La promoted hydrotalcite derived Ni-based catalysts: In situ preparation and CO₂ methanation performance. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 561-570. doi: 10.11862/CJIC.20230276
12. [12]
  Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081
13. [13]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
14. [14]
  Xiaofang Li , Zhigang Wang . Modulating d_z²-orbital occupancy of Au cocatalysts for enhanced photocatalytic H₂O₂ production. Acta Physico-Chimica Sinica, 2025, 41(7): 100080-. doi: 10.1016/j.actphy.2025.100080
15. [15]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005
16. [16]
  Siran Wang , Yinuo Wang , Yilong Zhao , Dazhen Xu . Advances in the Application and Preparation of Rhodanine and Its Derivatives. University Chemistry, 2025, 40(5): 318-327. doi: 10.12461/PKU.DXHX202407033
17. [17]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
18. [18]
  Xi YANG , Chunxiang CHANG , Yingpeng XIE , Yang LI , Yuhui CHEN , Borao WANG , Ludong YI , Zhonghao HAN . Co-catalyst Ni₃N supported Al-doped SrTiO₃: Synthesis and application to hydrogen evolution from photocatalytic water splitting. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 440-452. doi: 10.11862/CJIC.20240371
19. [19]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . 二维共价有机框架作为光催化剂在有机合成中的研究进展. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-. doi: 10.1016/j.actphy.2025.100086
20. [20]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(2361)
HTML views(493)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142