One-pot Synthesis of α,β-Dehydroamino Derivatives from β,β-Dicyanostyrene with 1,3-Dibromo-5,5-dimethylhydantoin Promoted by Mild Base

doi:10.1007/s40242-016-5233-4

Chemical Research in Chinese Universities ›› 2016, Vol. 32 ›› Issue (1): 68-75.doi: 10.1007/s40242-016-5233-4

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One-pot Synthesis of α,β-Dehydroamino Derivatives from β,β-Dicyanostyrene with 1,3-Dibromo-5,5-dimethylhydantoin Promoted by Mild Base

CHEN Zhanguo, DU Manfei, XIA Wei, HU Junli

Key Laboratory for Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, P. R. China

Received:2015-06-12 Revised:2015-07-15 Online:2016-02-01 Published:2015-09-21
Contact: CHEN Zhanguo E-mail:chzhg@snnu.edu.cn
Supported by:
Supported by the Natural Science Foundation of Shaanxi Province, China(No.2009JM2001), the Innovation Foundation of Postgraduate Cultivation of Shaanxi Normal University, China(No.2008CXB009) and the Fundamental Research Funds for the Central Universities of China(No.GK261001095).

Abstract

Abstract:

The reaction of β,β-dicyanostyrene derivatives(1) with 1,3-dibromo-5,5-dimethylhydantoin(DBDMH) was systematicly studied. The reaction could generate different products when promoted by different mild bases. When the reaction was promoted by NaOAc(100%, molar ratio to compound 1), β,β-dicyanostyrene derivatives could be directly converted into corresponding α,β-dehydroamino derivatives in good to excellent yields in one-pot. When the reaction was promoted by K₃PO₄(80%, molar ratio to compound 1), the corresponding α,β-dehydroamino and double-α,β-dehydroamino compounds were simultaneously obtained and the total conversion of β,β-dicyanostyrene derivatives was up to 90% or higher.

Key words: β,β-Dicyanostyrene derivative, 1,3-Dibromo-5,5-dimethylhydantoin(DBDMH), α,β-Dehydroamino

CHEN Zhanguo, DU Manfei, XIA Wei, HU Junli. One-pot Synthesis of α,β-Dehydroamino Derivatives from β,β-Dicyanostyrene with 1,3-Dibromo-5,5-dimethylhydantoin Promoted by Mild Base[J]. Chemical Research in Chinese Universities, 2016, 32(1): 68-75.

References

[1] Griffith D. A., Danishefsky S. J., J. Am. Chem. Soc., 1991, 113, 5863
[2] Barton D. H. R., Britten-Kelly M. R., Ferreira D., J. Chem. Soc., Perkin Trans. 1, 1978, 1090
[3] Driguez H., Vermes J. P., Lessard J., Can. J. Chem., 1978, 56, 119
[4] Lessard J., Driguez H., Vermes J. P., Tetrahedron Lett., 1970, 56, 4887
[5] Daniher F. A., Butler P. E., J. Org. Chem., 1968, 33, 4336
[6] Daniher F. A., Butler P. E., J. Org. Chem., 1968, 33, 2637
[7] Daniher F. A., Melchior M. T., Butler P. E., Chem. Commun., 1968, 931
[8] Seden T. P., Tuner R. W., J. Chem. Soc. C, 1968, 876
[9] He Z. T., Zhao Y. S., Tian P., Wang C. C., Dong H. Q., Lin G. Q., Org. Lett., 2014, 16, 1426
[10] Wu H. P., Hoge G., Org. Lett., 2004, 6, 3645
[11] Shultz C. S., Dreher S. D., Ikemoto N., Williams J. M., Grabowski E. J. J., Krska S. W., Sun Y., Dormer P. G., DiMichele L., Org. Lett., 2005, 7, 3405
[12] Ohashi A., Imamoto T., Org. Lett., 2001, 3, 373
[13] Yonehara K., Hashizume T., Mori K., Ohe K., Uemura S., J. Org. Chem., 1999, 64, 5593
[14] Trost B. M., Dake G. R., J. Am. Chem. Soc., 1997, 119, 7595
[15] Stohlmeyer M. M., Tanaka H., Wandless T. J., J. Am. Chem. Soc., 1999, 121, 6100
[16] Shibatomi K., Zhang Y., Yamamoto H., Chem. Asian J., 2008, 3, 1581
[17] He D. H., Zhu Y. C., Yang Z. R., Hu A. X., Cao G., Turk. J. Chem., 2009, 33, 393
[18] Chassaing C., Haudrechy A., Langlois Y., Tetrahedron Lett., 1997, 38, 4415
[19] Singh H., Gupta N., Kumar P., Dubey S. K., Sharma P. K., Organic Process Research & Development, 2009, 13, 870
[20] Yin Q., You S. L., Org. Lett., 2012, 14, 3526
[21] Chen Z. G., Hu J. L., Xia W., Wang D., Li Y. N., Chem. J. Chinese Universities, 2013, 34(5), 1151
[22] Söderman P., Widmalm G., Carbohydrate Research, 1999, 316, 184
[23] Maegawa T., Koutani Y., Otake K., Fujioka H., J. Org. Chem., 2013, 78, 3384
[24] Alam A., Takaguchi Y., Tsuboi S., Synthetic Commun., 2005, 35, 1329
[25] Chen Z. G., Wei J. F., Li R. T., Shi X. Y., Zhao P. F., J. Org. Chem., 2009, 74, 1371
[26] Chen Z. G., Wei J. F., Wang M. Z., Zhou L. Y., Zhang C. J., Shi X. Y., Adv. Synth. Catal., 2009, 351, 2358
[27] Wei J. F., Chen Z. G., Lei W., Zhang L. H., Wang M. Z., Shi X. Y., Li R. T., Org. Lett., 2009, 11, 4216
[28] Chen Z. G., Wang Y., Wei J. F., Zhao P. F., Shi X. Y., J. Org. Chem., 2010, 75, 2085
[29] Chen Z. G., Zhao P. F., Wang Y., Eur. J. Org. Chem., 2011, 5887
[30] Li G., Wei H. X., Kim S. H., Neighbors M., Org. Lett., 1999, 1, 395
[31] Li G., Wei H. X., Kim S. H., Org. Lett., 2000, 2, 2249
[32] Wei H. X., Kim S. H., Li G., Tetrahedron, 2001, 57, 3869
[33] Chen D., Timmons C., Chao S., Li G., Eur. J. Org. Chem., 2004, 3097
[34] Bach T., Schlummer B., Harms K., Chem. Commun., 2000, 287
[35] Klepacz A., Zwierzak A., Tetrahedron Lett., 2001, 42, 4539
[36] Liu Y. L., Liu D. E., Du M. F., Cao C. X., Chen Z. G., Chem. J. Chinese Universities, 2015, 36(6), 1117
[37] Chen Z. G., Liu Y. L., Hu J. L., Liu D. E., Chem. Res. Chinese Universities, 2015, 31(1), 65
[38] Chen Z. G., Wang D., Li Y. N., Wang Y. J., Hu J. L., Xia W., Acta Chim. Sinica, 2012, 70, 2236
[39] Chen Z. G., Wang Y. J., Liu D. E., Liu Y. L., LI Y. N., Wang D., Ge M., Chem. J. Chinese Universities, 2014, 35(7), 1458
[40] Wen H., Wang Y. J., Liu D. E., Liu Y. L., Ge M., Chen Z. G., Chin. J. Org. Chem., 2014, 34, 916
[41] Tu S. J., Rong L. C., Gao Y., Guo S. M., Lu S. H., Yang X. J., Chin. J. Org. Chem., 2002, 22, 364
[42] Islam M. M., Bhuiyan M. D. H., Bredow T., Try A. C., Computational and Theoryetical Chemistry, 2001, 967, 165

One-pot Synthesis of α,β-Dehydroamino Derivatives from β,β-Dicyanostyrene with 1,3-Dibromo-5,5-dimethylhydantoin Promoted by Mild Base

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