One-pot synthesis of α,β-dehydroamino derivatives from β,β-dicyanostyrene with 1,3-dibromo-5,5-dimethylhydantoin promoted by mild base

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.

Keywords

β,β-Dicyanostyrene derivative / 1,3-Dibromo-5,5-dimethylhydantoin(DBDMH) / α,β-Dehydroamino

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.