One-pot three-component Mannich reaction catalyzed by 2-hydroxylpyridine

Abstract

An effcient synthetic protocol for the β-amino carbonyl compounds was developed via one-pot three-component Mannich reaction of aromatic aldehydes, aromatic amines and cyclohexanone catalyzed by 2-hydroxylpyridine under mild reaction conditions. β-Amino carbonyl compounds were obtained in moderate to good yields and reasonable diastereoselectivities. The effects of different solvents, catalyst amounts and the scope of different substrates on the Mannich reactions were investigated. The plausible reaction mechanism was also discussed.

Keywords

2-Hydroxylpyridine / Catalyze / Mannich reaction / β-Amino carbonyl compound

References

[1] Azend M, Westermann B, Risch N. Angew. Chem. Int. Ed., 1998, 37: 1044.

[2] Córdova A. Acc. Chem. Res., 2004, 37(2): 102.

[3] Kobayashi S, Ishitani H. Chem. Rev., 1999, 99(5): 1069.

[4] Josephsohn N S, Carswell E L, Snapper M L, Hoveyda A H. Org. Lett., 2005, 7(13): 2711.

[5] Trost B M, Terrell L R. J. Am. Chem. Soc., 2003, 125(2): 338.

[6] Wu M, Jing H W, Chang T. Catal. Commun., 2007, 8: 2217.

[7] Li Z, Ma X, Liu J, Feng X, Tian G, Zhu A. J. Mol. Catal. A: Chem., 2007, 272: 132.

[8] Li H, Zeng H Y, Shao H W. Tetrahedron Lett., 2009, 50: 6858.

[9] Mukhopadhyay C, Datta A, Butcher R J. Tetrahedron Lett., 2009, 50: 4246.

[10] Guo Q, Liu H, Guo C, Luo S, Gu Y, Gong L. J. Am. Chem. Soc., 2007, 129(13): 3790.

[11] Azizi N, Torkiyan L, Saidi M R. Org. Lett., 2006, 8(10): 2079.

[12] Dziedzic P, Ibrahem I, Córdova A. Tetrahedron Lett., 2008, 49: 803.

[13] Teo Y, Lau J, Wu M. Tetrahedron: Asymmetry, 2008, 19: 186.

[14] Wang Y, Fu A P, Li H L, Tian F H, Yuan S P, Si H Z, Duan Y B, Wang Z H. Chem. Res. Chinese Universities, 2011, 27(4): 673.

[15] Wang L, Han J, Sheng J, Tian H, Fan Z. Catal. Commun., 2005, 6: 201.

[16] Fang D, Fei Z, Liu Z. Catal. Commun., 2009, 10: 1267.

[17] Sahoo S, Joseph T, Halligudi S B. J. Mol. Cata. A: Chem., 2006, 244: 179.

[18] Liu B Y, Zhao D S, Xu D Q, Xu Z Y. Chem. Res. Chinese Universities, 2007, 23(2): 163.

[19] Zhang H, Mifsud M, Tanaka F, Barbas C F. J. Am. Chem. Soc., 2006, 128(30): 9630.

[20] Kang Y K, Kim D Y. J. Org. Chem., 2009, 74(15): 5734.