Mannich reaction catalyzed by a novel catalyst under solvent-free conditions

Cai Bo Yue; Ting Feng Yi; Chuan Bing Zhu; Gang Liu

Journal of Industrial and Engineering Chemistry, Vol.15, No.5, 653-656, September, 2009

DOI10.1016/j.jiec.2009.09.038 Export Citation

Mannich reaction catalyzed by a novel catalyst under solvent-free conditions

Cai Bo Yue^†, Ting Feng Yi, Chuan Bing Zhu, and Gang Liu

School of Chemistry and Chemical Engineering, Anhui University of Technology, Maanshan 243002, China

E-mail:

An acidic catalyst [Py][CF3COO] (pyridinium trifluoroacetate) was synthesized and used in the Mannich reaction of various kinds of aromatic aldehydes, aromatic ketones and aromatic amines. β-Amino carbonyl compounds were obtained in reasonable yields when the Mannich reaction was carried out at room temperature under solvent-free conditions. The products could be separated from the catalyst simply via washing with water and after removing water, the catalyst could be recycled and reused for up to four times without noticeably decreasing in catalytic activity.

Keywords:Mannich reaction;Pyridinium trifluoroacetate;β-Amino carbonyl compounds;Solvent-free conditions

[References]

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Li Z, Ma XL, Liu J, Feng X, Tian GQ, Zhu AG, J. Mol. Catal. A-Chem., 272(1-2), 132 (2007)
Lin J, Zhang LF, Monatsh. Chem., 138, 77 (2007)
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[Referenced By]

[1] Tramontini M, Synthesis, 12, 703 (1973)

[2] Kleinmann EF, Comprehensive Organic Synthesis, Pergamon Press, New York (1991)

[3] Arend M, Westermann B, Risch N, Angew. Chem. Int. Ed., 37, 1044 (1998)

[4] Kobayashi S, Ueno M, Comprehensive Asymmetric Catalysis, Springer, Berlin (2004)

[5] Janey JM, Hsiao Y, Armstrong JD, J. Org. Chem., 71, 390 (2006)

[6] Itoh T, Nishimura K, Nagata K, Yokoya M, Synlett, 14, 2207 (2006)

[7] Yang JW, Stadler M, List B, Angew. Chem. Int. Ed., 46, 609 (2007)

[8] Liu BY, Xu DQ, Dong JF, Yang HL, Zhao DS, Luo SP, Xu ZY, Synth. Commun., 37, 3003 (2007)

[9] Guo GY, Yang T, Gao HX, Han BX, Huang J, Sun DH, Green Chem., 6, 75 (2004)

[10] Dong F, Jun L, Zhou XL, Liu ZL, Catal. Lett., 116(1-2), 76 (2007)

[11] Li JZ, Peng YQ, Song GH, Catal. Lett., 102(3-4), 159 (2005)

[12] Sahoo S, Joseph T, Halligudi SB, J. Mol. Catal. A-Chem., 244(1-2), 179 (2006)

[13] Yi WB, Cai C, J. Fluorine Chem., 127, 1515 (2006)

[14] Wang LM, Han JW, Sheng J, Tian H, Fan ZY, Catal. Commun., 6, 201 (2005)

[15] Wang LM, Han JW, Sheng J, Tian H, Chin. J. Org. Chem., 25, 591 (2005)

[16] Ollevier T, Nadeau E, Guay AA, Tetrahedron Lett., 47, 8351 (2006)

[17] Ollevier T, Nadeau E, J. Org. Chem., 69, 9292 (2004)

[18] Wang XX, Mao H, Yu Y, Zhu XD, Synth. Commun., 37, 3751 (2007)

[19] Shou WG, Yang YY, Wang YG, Tetrahedron Lett., 47, 1845 (2006)

[20] Loh TP, Chen SL, Org. Lett., 4, 3647 (2002)

[21] Loh TP, Liung SBKW, Tan KL, Wei LL, Tetrahedron, 56, 3227 (2000)

[22] Wang R, Li BG, Huang TK, Shi L, Lu XX, Tetrahedron Lett., 48, 2071 (2007)

[23] Li Z, Ma XL, Liu J, Feng X, Tian GQ, Zhu AG, J. Mol. Catal. A-Chem., 272(1-2), 132 (2007)

[24] Lin J, Zhang LF, Monatsh. Chem., 138, 77 (2007)

[25] Yi L, Lei HS, Zou JH, Xu XJ, Synthesis, 9, 717 (1991)

[26] Madhusudan SK, Misra AK, Carbohydr. Res., 340, 497 (2005)

[27] Akiyama T, Takaya J, Kagoshima H, Adv. Synth. Catal., 344, 338 (2002)