Chinese Journal of Organic Chemistry >
Efficient and Green Synthesis of 5-[(Indole-3-yl)-arylmethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione Derivatives in the Melt
Received date: 2016-01-10
Revised date: 2016-02-01
Online published: 2016-02-24
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).
An efficient melting method for the synthesis of β-indole derivatives via Yonemitsu reaction was developed successfully using aldehyde, indole and Meldrum's acid as the starting materials and 50 μL water as green promoter without other solvent. A series of 5-[(indole-3-yl)-arylmethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione derivatives were synthesized in 55%~94% yields. The remarkable advantages of this reaction were mild reaction condition, easy operation, tolerant the substrates with diverse functional groups and environment-friendly.
Lü Chengwei, Liu Yanhang, Zhou Xiaoxia . Efficient and Green Synthesis of 5-[(Indole-3-yl)-arylmethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione Derivatives in the Melt[J]. Chinese Journal of Organic Chemistry, 2016 , 36(6) : 1407 -1411 . DOI: 10.6023/cjoc201601010
[1] Feng, Y. D.; Zhang, H.; Cheng, G. L.; Cui, X. L. Chin. J. Org. Chem. 2014, 34, 1499 (in Chinese). (冯亚栋, 张红, 程国林, 崔秀灵, 有机化学, 2014, 34, 1499.)
[2] Tan, Y.; Luan, H. L.; Lin, H.; Sun, X. W.; Yang, X. D.; Dong, H. Q.; Lin, G. Q. Chem. Commun. 2014, 50, 10027.
[3] Ramesh, C.; Kavala, V.; Kuo, C. W.; Raju, B. R.; Yao, C. F. Eur. J. Org. Chem. 2010, 2010, 3796.
[4] Oikawa, Y.; Hirasawa, H.; Yonemitsu, O. Tetrahedron Lett. 1978, 20, 1759.
[5] Renzetti, A.; Dardennes, E.; Fontana, A.; Maria, P. D.; Sapi, J.; Gérard, S. J. Org. Chem. 2008, 73, 6824.
[6] Gérard, S.; Renzetti, A.; Lefevre, B.; Fontana, A.; Maria, P. D.; Sapi, J. Tetrahedron 2010, 66, 3065.
[7] Xu, Z. H.; Lin, C. H.; Liao, W. L. Chin. J. Appl. Chem. 2015, 32, 278 (in Chinese). (许招会, 林春花, 廖维林, 应用化学, 2015, 32, 278.)
[8] Xu, Z. H. Chin. J. Org. Chem. 2014, 34, 1687 (in Chinese). (许招会, 有机化学, 2014, 34, 1687.)
[9] Lin, C. H.; Xu, Z. H.; Liao, W. L.; Qiu, Z. Y.; Xia, J. H. Chin. J. Org. Chem. 2015, 35, 212 (in Chinese). (林春花, 许招会, 廖维林, 邱曾烨, 夏剑辉, 有机化学, 2015, 35, 212.)
[10] Liu, H. M.; Zhang, D. N.; Guo, X. M.; Li, H. Z. Chin. J. Synth. Chem. 2004, 12, 505 (in Chinese). (刘卉闵, 张冬暖, 果秀敏, 李慧章, 合成化学, 2004, 12, 505.)
[11] Armstrong, E. L.; Grover, H. K.; Kerr, M. A. J. Org. Chem. 2013, 78, 10534.
[12] Wang, C.; Li, G. S.; Li, J. C.; Zhang, Y. Q. Chem. Reag. 2003, 25, 369 (in Chinese). (王春, 李贵深, 李敬慈, 张英群, 化学试剂, 2003, 25, 369.)
[13] Wang, C.; Zhang, Y. Q.; Li, G. S.; Li, J. C.; Li, L. X. Chin. J. Org. Chem. 2003, 23, 1416 (in Chinese). (王春, 张英群, 李贵深, 李敬慈, 李晓陆, 有机化学, 2003, 23, 1416.)
[14] Yan, N.; Xia, J. H.; Xiong, Y. K.; Xiong, B.; Lin, C. H.; Liao, W. L. Chin. J. Org. Chem. 2014, 34, 2487 (in Chinese). (严楠, 夏剑辉, 熊云奎, 熊斌, 林春花, 廖维林, 有机化学, 2014, 34, 2487.)
[15] Yan, N.; Xiong, Y. K.; Xia, J. H.; Rui, P. X.; Lei, Z. W.; Liao, W. L.; Xiong, B. Chin. J. Org. Chem. 2015, 35, 384 (in Chinese). (严楠, 熊云奎, 夏剑辉, 芮培欣, 雷志伟, 廖维林, 熊斌, 有机化学, 2015, 35, 384.)
[16] Varma, R. S. Green Chem. 2014, 16, 2027.
[17] Schröder, K.; Matyjaszewski, K.; Noonan, K. J. T.; Mathers, R. T. Green Chem. 2014, 16, 1673.
[18] Reddy, M. V.; Kim, J. S.; Lim, K. T.; Jeong, Y. T. Tetrahedron Lett. 2014, 55, 6459.
[19] Nagarapu, L.; Mallepalli, R.; Kumar, U. N.; Venkateswarlu, P.; Bantu, R.; Yeramanchi, L. Tetrahedron Lett. 2012, 53, 1699.
[20] Li, C. J.; Chen, L. Chem. Soc. Rev. 2006, 35, 68.
[21] Appendino, G.; Cicione, L.; Minassi, A. Tetrahedron Lett. 2009, 50, 5559.
[22] Brahmachari, G. ACS Sustainable Chem. Eng. 2015, 3, 2350.
[23] Lyu, C. W.; Liu, Y. H.; Wang, J. J.; Zhou, X. X. Chin. J. Appl. Chem. 2015, 32, 1371 (in Chinese). (吕成伟, 刘妍杭, 王佳晶, 周晓霞, 应用化学, 2015, 32, 1371.)
[24] Bigi, F.; Carloni, S.; Ferrari, L.; Maggi, R.; Mazzacani, A.; Sartori, G. Tetrahedron Lett. 2001, 42, 5203.
[25] Maggi, R.; Bigi, F.; Carloni, S.; Mazzacani, A.; Sartori, G. Green Chem. 2001, 3, 173.
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