Citation: 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 shu

Three-Component Synthesis of 2-Oxazolines from Ethyl α-Cyanocinnamate Derivatives with Amides and N-Bromosuccinimide

1.
Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, ShaanxiNormal University, Xi'an 710119

Corresponding author: Chen Zhanguo, chzhg@snnu.edu.cn
Received Date: 18 March 2016
Revised Date: 22 April 2016

Fund Project: the Innovation Foundation of Postgraduate Cultivation of Shaanxi Normal University 2008CXB009the Natural Science Foundation of Shaanxi Province 2009JM2001the National Natural Science Foundation of China 20572066

Figures(3)

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.
- 2-oxazoline,
- ethyl α-cyanocinnamate,
- amide,
- N-bromosuccinimide
1. [1]
  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. [2]
  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. [3]
  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. [4]
  Frump, J. A. Chem. Rev. 1971, 71, 483. doi: 10.1021/cr60273a003
5. [5]
  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. [6]
  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. [7]
  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. [8]
  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. [9]
  Wuts, P. G. M.; Northuis, J. M.; Kwan, T. A. J. Org. Chem. 2000, 65, 9223. doi: 10.1021/jo000664r
10. [10]
  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. [11]
  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. [12]
  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. [13]
14. [14]
  Chen, Z. G.; Xia, W, ; Wen, H.; Wang, D.; Li, Y. N.; Hu, J. L. Chem. Res. Chin. Univ. 2013, 29, 699. doi: 10.1007/s40242-013-2420-4
15. [15]
  Li, W. L.; Chen, Z. G.; Zhou, J. M.; Hu, J. L.; Xia, W. Chin. J. Chem. 2012, 30, 830. doi: 10.1002/cjoc.201100346
16. [16]
  Sun, Q.; Shi, L. X.; Ge, Z. M.; Cheng, T. M.; Li, R. T. Chin. J. Chem. 2005, 23, 745. doi: 10.1002/(ISSN)1614-7065
17. [17]
  Rao, P. S.; Venkataratnam, R. V. Tetrahedron Lett. 1991, 32, 5821. doi: 10.1016/S0040-4039(00)93564-0
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沈阳化工大学材料科学与工程学院沈阳 110142