Chinese Journal of Organic Chemistry >
Three-Component Synthesis of 2-Oxazolines from Ethyl α-Cyanocinnamate Derivatives with Amides and N-Bromosuccinimide
Received date: 2016-03-18
Revised date: 2016-04-22
Online published: 2016-05-06
Supported by
Project supported by the National Natural Science Foundation of China (No.20572066), the Natural Science Foundation of Shaanxi Province (No.2009JM2001) and the Innovation Foundation of Postgraduate Cultivation of Shaanxi Normal University (No.2008CXB009).
An easy and efficient new method for the three-component synthesis of 2-oxazolines from ethyl α-cyanocinnamate derivatives with amide and N-bromosuccinimide has been developed. A series of ethyl α-cyanocinnamate derivatives can be smoothly con-verted into corresponding 2-oxazoline derivatives promoted by Na2CO3 in N,N-dimethylformamide (DMF) at room temperature in high yield (up to 94%). The reactions of 11 structurally different substrates with propionamide, acrylamide, isobutyamide and pentanamide were investigated, respectively. The results indicated that the protocol has applicability in a large scope of ethyl α-cyanocinnamate derivatives and amides. A possible mechanism was proposed and it can explain well the full regiospecificity of the reaction. 39 new compounds were achieved via the three-component synthesis reaction and all the products structures were confirmed by their 1H NMR, 13C NMR and HRMS analysis.
Key words： 2-oxazoline; ethyl α-cyanocinnamate; amide; N-bromosuccinimide
Chen Zhanguo , Hou Dan , Liu De'e , Hui Wenping . Three-Component Synthesis of 2-Oxazolines from Ethyl α-Cyanocinnamate Derivatives with Amides and N-Bromosuccinimide[J]. Chinese Journal of Organic Chemistry, 2016 , 36(9) : 2191 -2196 . DOI: 10.6023/cjoc201603032
[1] (a) Braga, A. L.; Galetto, F. Z.; Taube, P. S.; Paixão, M. W.; Silveira, C. C.; Singh, D.; Vargas, F. J. Organomet. Chem. 2008, 693, 3563. (b) Lee, S.-H.; Bok, J.; Qi, X.; Kim, S. K.; Leed, Y.-S.; Yoon, J. Tetrahedron Lett. 2007, 48, 7309. (c) Yang, D.; Yip, Y. C.; Wang, X. C. Tetrahedron Lett. 1997, 38, 7083. (d) Reddy, L. R.; Saravanan, P.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 6230.
[2] (a) Saravanan, P.; Corey, E. J. J. Org. Chem. 2003, 68, 2760. (b) Kobayashi, S.; Fujikawa, S.-I.; Ohmae, M. J. Am. Chem. Soc. 2003, 125, 14357. (c) Sone, H.; Kigoshi, H.; Yamada, K. Tetrahedron, 1997, 53, 8149. (d) Kingston, D. G. I.; Chaudhary, A. G.; Gunatilaka, A. A. L.; Middleton, M. L. Tetrahedron Lett. 1994, 35, 4483.
[3] (a) Hargaden, G. C.; Guiry, P. J. Chem. Rev. 2009, 109, 2505. (b) Desimoni, G.; Faita, G.; Jørgensen, K. A. Chem. Rev. 2006, 106, 3561.
[4] Frump, J. A. Chem. Rev. 1971, 71, 483.
[5] (a) Kangani, C. O.; Day, B. W. Tetrahedron Lett. 2009, 50, 5332. (b) Kangani, C. O.; Kelley, D. E. Tetrahedron Lett. 2005, 46, 8917. (c) Crosignani, S.; Swinnen, D. J. Comb. Chem. 2005, 7, 688. (d) Wipf, P.; Wang, X. D. J. Comb. Chem. 2002, 4, 656.
[6] (a) Zhou, P. W.; Blubaum, J. E.; Bums, C. T. Tetrahedron Lett. 1997, 38, 7019. (b) Hǒlderle, M.; Bar, G.; Mlhaupt, R. J. Polym. Sci., Part. A:Polym. Chem. 1997, 35, 2539. (c) Ohshima, T.; Iwasaki, T.; Mashima, K. Chem. Commun. 2006, 2711.
[7] (a) Mei, L.; Hai, Z. J.; Jie, S.; Ming, S.; Hao, Y.; Liang, H. K. J. Comb. Chem. 2009, 11, 220. (b) Baltork, I. M.; Moghadam, M.; Tangestaninejad, S. Catal. Commun. 2008, 9, 1153. (c) Baltork, I. M.; Khosropour, A. R.; Hojati, S. F. Catal. Commun. 2007, 8, 2000. (d) Jnaneshwara, G. K.; Deshpande, V. H.; Lalithambika, M.; Ravindranathan, T.; Bedekar, A. V. Tetrahedron Lett. 1998, 39, 459.
[8] (a) Chaudhry, P.; Schoenen, F.; Neuenswander, B. J. Comb. Chem. 2007, 9, 473. (b) Schwekendiek, K.; Glorius, F. Synthesis 2006, 2996. (c) Badiang, J. G.; Aubé, J. J. Org. Chem. 1996, 61, 2484.
[9] Wuts, P. G. M.; Northuis, J. M.; Kwan, T. A. J. Org. Chem. 2000, 65, 9223.
[10] (a) Hajra, S.; Bar, S.; Sinha, D.; Maji, B. J. Org. Chem. 2008, 73, 4320. (b) Minakata, S.; Morino, Y.; Ide, T. Chem. Commun. 2007, 3279. (c) Yeung, Y. Y.; Gao, X.; Corey, E. J. A. J. Am. Chem. Soc. 2006, 128, 9644. (d) Nishimura, M.; Minakata, S.; Takahashi, T.; Oderaotoshi, Y.; Komatsu, M. J. Org. Chem. 2002, 67, 2101. (e) Minakata, S.; Nishimura, M.; Takahashi, T.; Oderaotoshi, Y.; Komatsu, M. Tetrahedron Lett. 2001, 42, 9019.
[11] (a) Pei, W.; Timmons, C.; Xu, X.; Wei, H.-X.; Li, G. Org. Biomol. Chem. 2003, 1, 2919. (b) Wei, H.-X.; Kim, S. H.; Li, G. J. Org. Chem. 2002, 67, 4777. (c) Chen, D.-J.; Timmons, C.; Wei, H.-X.; Li, G. J. Org. Chem. 2003, 68, 5742. (d) Pei, W.; Wei, H.-X.; Chen, D.-J.; Headley, A. D.; Li, G. J. Org. Chem. 2003, 68, 8404.
[12] (a) Liu, X.-G.; Wei, Y.; Shi, M. Eur. J. Org. Chem. 2010, 1977. (b) Anabha, E.; Raveendran, R. R.; Paul, E. S.; Vijay, N. Org. Biomol. Chem. 2010, 8, 901. (c) Kawai, D.; Kawasumi, K.; Miyahara, T.; Hirashita, T.; Araki, S. Tetrahedron 2009, 65, 10390. (d) Nair, V.; Babu, B. P.; Varghese, V.; Sinu, C. R.; Paul, R. R.; Anabha, E. R.; Suresh, E. Tetrahedron Lett. 2009, 50, 3716.
[13] (a) Chen, Z. G.; Wang, Y.; Wei, J. F.; Zhao, P. F.; Shi, X. Y. J. Org. Chem. 2010, 75, 2085. (b) Chen, Z. G.; Zhou, J. M.; Wang, Y.; Li, W. L. Acta Chim. Sinica 2011, 69, 2851(in Chinese). (陈战国, 周继梅, 王芸, 李文丽, 化学学报, 2011, 69, 2851.) (c) Chen, Z. G.; Zhao, P. F.; Wang, Y. Eur. J. Org. Chem. 2011, 5887. (d) Li, W. L.; Chen, Z. G.; Zhou, J. M.; Hu, J. L.; Xia, W. Chin. J. Chem. 2012, 30, 830. (e) Wen, H.; Wang, Y. J.; Liu, D. E.; Liu, Y. L.; Ge, M.; Chen, Z. G. Chin. J. Org. Chem. 2014, 34, 916(in Chinese). (闻化, 王英杰, 刘德娥, 刘亚丽, 葛淼, 陈战国, 有机化学, 2014, 34, 916.) (f) Wei, J. F.; Chen, Z. G.; Gao, Y. N.; Zhang, P.; Wang, C. N.; Zhao, P. F.; Wang, Y.; Shi, X. Y. Chin. J. Chem. 2012, 30, 391. (g) Chen, Z. G.; Wei, J. F.; Li, R. T.; Shi, X. Y.; Zhao, P. F. J. Org. Chem. 2009, 74, 1371. (h) Chen, Z. G.; Zhou, L. Y.; Li, W. L.; Zhou, J. M.; Wang, C. N. Acta Chim. Sinica 2011, 69, 1093(in Chinese). (陈战国, 周利燕, 李文丽, 周继梅, 王传宁, 化学学报, 2011, 69, 1093.) (i) Chen, Z. G.; Wang, D.; Li, Y. N.; Wang, Y. J.; Hu, J. L.; Xia, W. Acta Chim. Sinica 2012, 70, 2236(in Chinese). (陈战国, 王丹, 李亚男, 王英杰, 胡均利, 夏伟, 化学学报, 2012, 70, 2236.) (j) Chen, Z. G.; Wei, J. F.; Wang, M. Z.; Zhou, L. Y.; Zhang, C. J.; Shi, X. Y. Adv. Synth. Catal. 2009, 351, 2358.
[14] Chen, Z. G.; Xia, W,; Wen, H.; Wang, D.; Li, Y. N.; Hu, J. L. Chem. Res. Chin. Univ. 2013, 29, 699.
[15] Li, W. L.; Chen, Z. G.; Zhou, J. M.; Hu, J. L.; Xia, W. Chin. J. Chem. 2012, 30, 830.
[16] Sun, Q.; Shi, L. X.; Ge, Z. M.; Cheng, T. M.; Li, R. T. Chin. J. Chem. 2005, 23, 745.
[17] Rao, P. S.; Venkataratnam, R. V. Tetrahedron Lett. 1991, 32, 5821.
/
| 〈 |
|
〉 |
