Synthesis of 2-oxazolines from ethyl α-cyanocinnamate derivatives with acetamide and N-bromosuccinimide

Abstract

An efficient method for the one-pot synthesis of 2-oxazolines from ethyl α-cyanocinnamate derivatives with acetamide and N-bromosuccinimide(NBS) in the presence of K₃PO₄ was developed. The reaction was performed smoothly and cleanly to give 2-oxazolines in good to excellent yields(up to 95%) in acetone at room temperature. Thirteen examples were investigated and the results indicated that a large range of α-cyanocinnamate derivatives could be suitable for this method. Based on the outcomes of experiment, a possible consecutive nucleophilic addition-cyclization pathway was proposed.

Keywords

One-pot synthesis / Oxazoline / Acetamide / N-Bromosuccinimide(NBS) / Regioselectivity / Nucleophilic addition-cyclization

References

[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.

[2] Lee S H, Bok J, Qi X, Kim S K, Leed Y S, Yoon J. Tetrahedron Lett., 2007, 48: 7309.

[3] Yang D, Yip Y C, Wang X C. Tetrahedron Lett., 1997, 38: 7083.

[4] Reddy L R, Saravanan P, Corey E J A. J. Am. Chem. Soc., 2004, 126: 6230.

[5] Saravanan P, Corey E J A. J. Org. Chem., 2003, 68: 2760.

[6] Kobayashi S, Fujikawa S I, Ohmae M. J. Am. Chem. Soc., 2003, 125: 14357.

[7] Sone H, Kigoshi H, Yamada K. Tetrahedron, 1997, 53: 8149.

[8] Kingston D G I, Chaudhary A G, Gunatilaka A A L, Middleton M L. Tetrahedron Lett., 1994, 35: 4483.

[9] Li Y J, Li C Y, Jin K, Sun S Q, Zhou X X. Acta Chim. Sinica, 2012, 70: 151.

[10] Hargaden G C, Guiry P. J. Chem. Rev., 2009, 109: 2505.

[11] Desimoni G, Faita G, Jørgensen K A. Chem. Rev., 2006, 106: 3561.

[12] Allen J V, Williams J M J. Tetraheron: Asymmetry, 1994, 5: 277.

[13] Zhang W, Hirao T, Ikeda I. Tetrahedron Lett., 1996, 37: 4545.

[14] Phaltz A. Acta Chem. Scand., 1996, 50: 189.

[15] Helmchen G, Kudis S, Sennhenn P, Steinhagen H. Pure Appl. Chem., 1997, 119: 7893.

[16] Greene T W, Wuts P G M. Protective Groups in Organic Synthesis, 1999 3rd. Ed. New York: Wiley 293.

[17] Frump J A. Chem. Rev., 1971, 71: 483.

[18] Kangani C O, Day B W. Tetrahedron Lett., 2009, 50: 5332.

[19] Kangani C O, Kelley D E. Tetrahedron Lett., 2005, 46: 8917.

[20] Crosignani S, Swinnen D. J. Comb. Chem., 2005, 7: 688.

[21] Wipf P, Wang X D. J. Comb. Chem., 2002, 4: 656.

[22] Zhou P W, Blubaum J E, Bums C T. Tetrahedron Lett., 1997, 38: 7019.

[23] Holderle M, Bar G, Mlhaupt R. J. Polym. Sci. Part A: Polym. Chem., 1997, 35: 2539.

[24] Ohshima T, Iwasaki T, Mashima K. Chem. Commun., 2006, 25: 2711.

[25] Mei L, Hai Z J, Jie S, Ming S, Hao Y, Liang H K. J. Comb. Chem., 2009, 11: 220.

[26] Baltork M I, Moghadam M, Tangestaninejad S. Catal. Commun., 2008, 9: 1153.

[27] Baltork I M, Khosropour A R, Hojati S F. Catal. Commun., 2007, 8: 2000.

[28] Jnaneshwara G K, Deshpande V H, Lalithambika M, Ravindranathan T, Bedekar AV. Tetrahedron Lett., 1998, 39: 459.

[29] Chaudhry P, Schoenen F, Neuenswander B. J. Comb. Chem., 2007, 9: 473.

[30] Schwekendiek K, Glorius F. Synthesis, 2006, 18: 2996.

[31] Badiang J G, Aubé J. J. Org. Chem., 1996, 61: 2484.

[32] Oussaid B, Berlan J, Soufiaoui M, Garrigues B. Synth.Commun., 1995, 25: 659.

[33] Wuts P G M, Northuis J M, Kwan T A. J. Org. Chem., 2000, 65: 9223.

[34] Sakakura A, Kondo R, Ishihara K. Org. Letter., 2005, 7: 1971.

[35] Crosignani S, Young A C, Linclau B. Tetrahedron Lett., 2004, 45: 9611.

[36] Phillips J A, Uto Y, Wipf P, Reno M J, Williams D R. Org. Letter, 2000, 2: 1165.

[37] Pirrung M C, Tumey L N. J. Comb. Chem., 2000, 2: 675.

[38] Wipf P, Venkatraman S. Tetrahedron Lett., 1996, 37: 4659.

[39] Hajra S, Bar S, Sinha D, Maji B. J. Org. Chem., 2008, 73: 4320.

[40] Minakata S, Morino Y, Ide T. Chem. Commun., 2007, 31: 3279.

[41] Yeung Y Y, Gao X, Corey E J A. J. Am. Chem. Soc., 2006, 128: 9644.

[42] Nishimura M, Minakata S, Takahashi T, Oderaotoshi Y, Komatsu M. J. Org. Chem., 2002, 67: 2101.

[43] Minakata S, Nishimura M, Takahashi T, Oderaotoshi Y, Komatsu M. Tetrahedron Lett., 2001, 42: 9019.

[44] Liu X G, Wei Y, Shi M. Eur. J. Org. Chem., 2010, 1977.

[45] Anabha E, Raveendran R R, Paul E S, Vijay N. Org. Biomol. Chem., 2010, 8: 901.

[46] Kawai D, Kawasumi K, Miyahara T, Hirashita T, Araki S. Tetrahedron, 2009, 65: 10390.

[47] Nair V, Babu B P, Varghese V, Sinu C R, Paul R R, Anabha E R, Suresh E. Tetrahedron Letters, 2009, 50: 3716.

[48] Chen Z G, Wang Y, Wei J F, Zhao P F, Shi X Y. J. Org. Chem., 2010, 75: 2085.

[49] Chen Z G, Zhou J M, Wang Y, Li W L. Acta Chim. Sinica, 2011, 69: 2851.

[50] Chen Z G, Zhao P F, Wang Y. Eur. J. Org. Chem., 2011, 5887.

[51] Qian Y, Ji X Y, Zhou W, Han J L, Li G, Pan Y. Tetrahedron, 2012, 68: 6198.

[52] Chen Z G, Wei J F, Li W L, Wang Y, Zhao P F, Shi X Y. Chin. J. Chem., 2011, 29: 1689.

[53] Ji X Y, Mei H B, Qian Y, Han J L, Li G, Pan Y. Synthesis, 2011, 3680.

[54] Chen Z G, Wei J F, Li R T, Shi X Y, Zhao P F. J. Org. Chem., 2009, 74: 1371.

[55] Zhi S J, Mei H B, Zhang G Q, Sun H, Han J L, Li G, Pan Y. Science China: Chemistry, 2010, 53: 1946.

[56] Chen Z G, Zhou L Y, Li W L, Zhou J M, Wang C N. Acta Chim. Sinica, 2011, 69: 1093.

[57] Chen Z G, Wei J F, Wang M Z, Zhou L Y, Zhang C J, Shi X Y. Adv. Synth. Catal., 2009, 351: 2358.

[58] Zhi S J, Sun H, Zhang G Q, Li G, Pan Y. Org. Biomol. Chem., 2010, 8: 628.

[59] Bourguignon J, Le Nard G, Queguiner G. Can. J. Chem., 1985, 63: 2354.

[60] McAnda A F, Roberts K D, Smallridge A J, Ten A, Trewhella M A. J. Chem. Soc., Perkin Trans. 1, 1998, 501.

[61] Liu J T, Yao C F. Tetrahedron Lett., 2001, 42: 6147.

[62] Bowman R K, Johnson J S. J. Org. Chem., 2004, 69: 8537.