N-溴代丁二酰亚胺催化水杨醛与麦氏酸反应合成香豆素-3-羧酸
收稿日期: 2017-01-05
修回日期: 2017-03-21
网络出版日期: 2017-04-18
基金资助
国家自然科学基金(No.21403100)和辽宁省博士启动基金(No.20141100)资助项目.
N-Bromosuccinimide Mediated the Reaction of 2-Hydroxyaryl Aldehydes with Meldrum's Acid for Synthesis of Coumarin-3-carboxylic Acids
Received date: 2017-01-05
Revised date: 2017-03-21
Online published: 2017-04-18
Supported by
Project supported by the National Natural Science Foundation of China (No. 21403100) and the Doctoral Scientific Research Foundation of Liaoning Province (No. 20141100).
阮鸿力, 张婧圆, 孙赛, 杨颖, 朱小磊, 吕成伟 . N-溴代丁二酰亚胺催化水杨醛与麦氏酸反应合成香豆素-3-羧酸[J]. 有机化学, 2017 , 37(8) : 2139 -2144 . DOI: 10.6023/cjoc201701003
A N-bromosuccinimide (NBS) promoted procedure for the synthesis of coumarin-3-carboxylic acids via Knoevenagel-intramolecular cyclization cascade reaction of Meldrum's acid with various 2-hydroxyarylaldehydes has been developed. Using the mixture of water and ethanol as solvent, employing inexpensive NBS as the catalyst, and reacted at room temperature are found to highly applicable to get a satisfactory outcome. This approach expands the method for the preparation of coumarin-3-carboxylic acids and also provides other features such as mild reaction conditions, tolerant the substrates with diverse functional groups, simple workup procedure and easy isolation.
[1] Safaei, H. R.; Safaei, M.; Shekouhy, M. RSC Adv. 2015, 5, 6797.
[2] Dekamin, M. G.; Eslami, M. Green Chem. 2014, 16, 4914.
[3] Xiong, X.; Han, Q.; Shi, L.; Xiao, S.; Bi, C. Chin. J. Org. Chem. 2016, 36, 480(in Chinese). (熊兴泉, 韩骞, 石霖, 肖上运, 毕成, 有机化学, 2016, 36, 480.)
[4] Wei, L.; Chen, X.; Liu, Y.; Wan, J. Chin. J. Org. Chem. 2016, 36, 954(in Chinese). (韦丽, 陈绪文, 刘云云, 万结平, 有机化学, 2016, 36, 954.)
[5] Zhang, Q.; Vigier, K. D. O.; Royer, S.; Jérôme, F. Chem. Soc. Rev. 2012, 41, 7108.
[6] Patil, D.; Chandam, D.; Mulik, A.; Patil, P.; Jagadale, S.; Kant, R.; Gupta, V.; Deshmukh, M. Catal. Lett. 2014, 144, 949.
[7] Brahmachari, G.; Banerjee, B. ACS Sustainable Chem. Eng. 2014, 2, 411.
[8] Chandam, D. R.; Mulik, A. G.; Patil, P. P.; Jagdale, S. D.; Patil, D. R.; Deshmukh, M. B. Res. Chem. Intermed. 2015, 41, 761.
[9] Shabalala, N.; Maddila, S.; Jonnalagadda, S. B. New J. Chem. 2016, 40, 5107.
[10] Adib, M.; Yasaei, Z.; Mirzaei, P. Synlett 2016, 27, 383.
[11] Venkatesan, K.; Pujari, S. S.; Srinivasan, K. V. Synth. Commun. 2009, 39, 228.
[12] Ghosh, S.; Das, J.; Chattopadhyay, S. Tetrahedron Lett. 2011, 52, 2869.
[13] Sadeh, F. N.; Maghsoodlou, M. T.; Hazeri, N.; Kangani, M. Res. Chem. Intermed. 2015, 41, 5907.
[14] Sui, X. -F.; Yuan, J. -Y.; Zhou, M.; He, Y. -H. Chin. J. Org. Chem. 2006, 26, 1518(in Chinese). (隋晓锋, 袁金颖, 周密, 何永洪, 有机化学, 2006, 26, 1518.)
[15] Xu, D.; Wang, S.; Shen, Z.; Xia, C.; Sun, W. Org. Biomol. Chem. 2012, 10, 2730.
[16] Liu, W.; Chen, C.; Qiu, H. Chin. J. Org. Chem. 2015, 35, 450(in Chinese). (刘卫兵, 陈翠, 邱会华, 有机化学, 2015, 35, 450.)
[17] Saikia, I.; Borah, A. J.; Phukan, P. Chem. Rev. 2016, 116, 6837.
[18] Shinde, M. H.; Kshirsagar, U. A. Green Chem. 2016, 18, 1455.
[19] Talluri, S. K.; Sudalai, A. Org. Lett. 2005, 7, 855.
[20] Ghorbani-Vaghei, R.; Malaekehpoor, S. M. Tetrahedron Lett. 2012, 53, 4751.
[21] Kiyani, H.; Kanaani, A.; Ajloo, D.; Ghorbani, F.; Vakili, M. Res. Chem. Intermed. 2015, 41, 7739.
[22] Xiong, M.; Xi, H.; Fu, Y.; Sun, X. Chin. J. Org. Chem. 2010, 30, 908(in Chinese). (熊敏秋, 席海涛, 付永胜, 孙小强, 有机化学, 2010, 30, 908.)
[23] Wang, H.; Zheng, W.; Xie F.; Song, H. Chin. J. Org. Chem. 2011, 31, 708(in Chinese). (王辉, 郑伟华, 谢凤妮, 宋化灿, 有机化学, 2011, 31, 708.)
[24] Wei, J.; Wang, P.; Jia, Q.; Huang, J.; Du, Z.; Zhang, K.; Wang, J. Eur. J. Org. Chem. 2013, 2013, 4499.
[25] Sandhu, S.; Bansal, Y.; Silakari, O.; Bansal, G. Bioorg. Med. Chem. 2014, 22, 3806.
[26] Niharika, P.; Ramulu, B. V.; Satyanarayana, G. Org. Biomol. Chem. 2014, 12, 4347.
[27] Li, C.; Yang, D.; Yin, 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.)
[28] He, X.; Yan, Z.; Hu, X.; Zuo, Y.; Jiang, C.; Jin, L.; Shang, Y. Synth. Commun. 2014, 44, 1507.
[29] Rahmani-Nezhad, S.; Khosravani, L.; Saeedi, M.; Divsalar, K.; Firoozpour, L.; Pourshojaei, Y.; Sarrafi, Y.; Nadri, H.; Moradi, A.; Mahdavi, M.; Shafiee, A.; Foroumadi, A. Synth. Commun. 2015, 45, 741.
[30] Vekariya, R. H.; Patel, H. D. Synth. Commun. 2014, 44, 2756.
[31] Undale, K. A.; Gaikwad, D. S.; Shaikh, T. S.; Desai, U. V.; Pore, D. M. Indian J. Chem., Sect. B 2012, 51B, 1039.
[32] Yang, G.; Wang, C.; Fan, S.; Xie, P.; Jin, Q.; Xu, C. Chin. J. Org. Chem. 2015, 35, 1173(in Chinese).(杨国玉, 王彩霞, 樊素芳, 谢普会, 金秋, 徐翠莲, 有机化学, 2015, 35, 1173.)
[33] Scott, J. L.; Raston, C. L. Green Chem. 2000, 2, 245.
[34] Alvim, J.; Dias, Jr., R. L. A.; Castilho, M. S.; Oliva, G.; Corrêa, A. G. J. Braz. Chem. Soc. 2005, 16, 763.
[35] Heravi, M. M.; Sadjadi, S.; Oskooie, H. A.; Shoar, R. H.; Bamoharram, F. F. Catal. Commun. 2008, 9, 470.
[36] Li, Y.; Gao, W. Synth. Commun. 2012, 42, 2067.
[37] Karami, B.; Farahi, M.; Khodabakhshi, S. Helv. Chim. Acta 2012, 95, 455.
[38] He, X.; Shang, Y.; Zhou, Y.; Yu, Z.; Han, G.; Jin, W.; Chen, J. Tetrahedron 2015, 71, 863.
[39] Fiorito, S.; Genovese, S.; Taddeo, V. A.; Epifano, F. Tetrahedron Lett. 2015, 56, 2434.
[40] Brahmachari, G. ACS Sustainable Chem. Eng. 2015, 3, 2350.
[41] Chavan, H. V.; Bandgar, B. P. ACS Sustainable Chem. Eng. 2013, 1, 929.
[42] Fiorito, S.; Taddeo, V. A.; Genovese, S.; Epifano, F. Tetrahedron Lett. 2016, 57, 4795.
[43] Pan, W. -Y.; Xiao, Y. -M.; Xiong, H. -Q.; Lü, C. -W. Res. Chem. Intermed. 2016, 42, 7057.
[44] Gao, S.; Xiao, D.; Yang, Y.; Wei, X.; Sun, S.; Lang, J.; Lv, C. Heterocycles 2016, 92, 1698.
[45] Bigi, F.; Carloni, S.; Ferrari, L.; Maggi, R.; Mazzacani, A.; Sartori, G. Tetrahedron Lett. 2001, 42, 5203.
/
〈 |
|
〉 |