一种新的无催化剂条件下的2,3-喹啉二羧酸酯的合成
收稿日期: 2017-08-25
修回日期: 2017-10-11
网络出版日期: 2017-10-24
基金资助
国家自然科学基金（Nos.21402068，21574060，21472177）资助项目.
A New Catalyst-Free Synthesis of 2,3-Dicarboxylic Ester Quinoline Derivatives
Received date: 2017-08-25
Revised date: 2017-10-11
Online published: 2017-10-24
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21402068, 21574060, 21472177).
王彬 , 叶文波 , 晏子聪 , 万常峰 , 侯豪情 , 汪志勇 . 一种新的无催化剂条件下的2,3-喹啉二羧酸酯的合成[J]. 有机化学, 2018 , 38(2) : 504 -508 . DOI: 10.6023/cjoc201708054
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.
Key words： quinoline derivatives; catalyst-free; green synthesis
[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.
[2] Nayyar, A.; Malde, A.; Jain, R.; Coutinho, E. Bioorg. Med. Chem. 2006, 14, 7302.
[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.
[4] Baba, A.; Kawamura, N.; Makino, H.; Ohta, Y.; Taketomi, S.; Sohda, T. J. Med. Chem. 1996, 39, 5176.
[5] Muruganantham, N.; Sivakumar, R.; Anbalagan, N.; Gunasekaran, V.; Leonard, J. T. Biol. Pharm. Bull. 2004, 27, 1683.
[6] Nayyar, A.; Malde, A.; Coutinho, E.; Jain, R. Bioorg. Med. Chem. 2006, 14, 7302.
[7] Pharmacopoeia Committee of the People's Republic of China Ministry of Health Pharmacopoeia of the People's Republic of China•Pharmacopoeia Annotation, Chemical Industry Press, Beijing, 1990, p. 963(in Chinese). (中华人民共和国卫生部药典委员会, 中华人民共和国药典•药典注释, 化学工业出版社, 北京, 1990, p. 963.)
[8] (a) Zouhiri, F.; Danet, M.; Benard, C.; Normand-Bayle, M.; Mouscadet, J. F.; Leh, H.; Thomas, C. M.; Mbemba, G.; d'Angelo, J.; Desmaele, D.
(b) Du, D.; Fang, J. Chin. J. Org. Chem. 2007, 27, 1318(in Chinese). (杜鼎, 方建新, 有机化学, 2007, 27, 1318.)
[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] Combes, A. Bull. Soc. Chim. Fr. 1888, 49, 89.
[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] Chanda, T.; Verma, R. K.; Singh, M. S. Chem. -Asian J. 2012, 7, 778.
[13] (a) Pandit, R. P.; Lee, Y. R. RSC Adv. 2013, 3, 22039.
(b) Bagdi, A. K.; Santra, S.; Rahman, M.; Majee, A.; Hajra, A. RSC Adv. 2013, 3, 24034.
[14] Venkanna, A.; Swapn, K.; Rao, P. V. RSC Adv. 2014, 4, 15154.
[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] (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] (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] (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.
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