Citation: Mir Rasul Mousavi, Nourallah Hazeri, Malek Taher Maghsoodlou, Sajjad Salahi, Sayyed Mostafa Habibi-Khorassani. Entirely green protocol for the synthesis of β-aminoketones using saccharose as a homogenous catalyst[J]. Chinese Chemical Letters, ;2013, 24(05): 411-414. shu

Entirely green protocol for the synthesis of β-aminoketones using saccharose as a homogenous catalyst

1.
Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674, Zahedan, Iran

Corresponding author: Nourallah Hazeri,
Received Date: 11 January 2013
Available Online: 5 March 2013

Saccharose was applied as an efficient and homogenous catalyst for a one-pot, three-component Mannich reaction for the formation of β-aminoketones from aromatic aldehydes, anilines, and acetophenone at ambient temperature in excellent yields. This protocol has the following advantages: mild conditions, high yields, clean reaction profiles, operational simplicity, and environmentally benign and simple work-up procedures.
- Saccharose,
- β-Amino carbonyl compounds,
- Mannich reaction,
- Three-component reaction
1. [1]
  [1] C. Mannich, W. Krosche, Ueber ein kondensationsprodukt aus formaldehyd, ammoniak und antipyrin, Arch. Pharm. 250 (1912) 647-667.
2. [2]
  [2] M. Suginome, L. Uehlin, M. Murakami, Aminoboranes as "compatible" iminium ion generators in aminative C-C bond formations, J. Am. Chem. Soc. 126 (2004) 13196-13197.
3. [3]
  [3] W. Notz, F. Tanaka, S.I. Watanabe, et al., The direct organocatalytic asymmetric Mannich reaction: unmodified aldehydes as nucleophiles, J. Org. Chem. 68 (2003) 9624-9634.
4. [4]
  [4] R. Muller, H. Goesmann, H. Waldmann, N,N-phthaloylamino acids as chiral auxiliaries in asymmetric Mannich-type reactions, Angew. Chem. Int. Ed. 38 (1999) 184-187.
5. [5]
  [5] F.A. Davis, J.M. Szewczyk, Synthesis and applications of nonracemic b-amino aldehydes to the asymmetric synthesis of piperdines: (+)-dihydropinidine, Tetrahedron Lett. 39 (1998) 5951-5954.
6. [6]
  [6] S. Sahoo, T. Joseph, S.B. Halligudi, Mannich reaction in Brönsted acidic ionic liquid: a facile synthesis of β-amino carbonyl compounds, J. Mol. Catal. A: Chem. 244 (2006) 179-182.
7. [7]
  [7] X.C. Wang, L.J. Zhang, Z. Zhang, Z.J. Quan, PEG-OSO₃H as an efficient and recyclable catalyst for the synthesis of β-amino carbonyl compounds via the Mannich reaction in PEG-H2O, Chin. Chem. Lett. 23 (2012) 423-426.
8. [8]
  [8] Y. Dai, B.D. Li, H.D. Quan, C.X. Lu, CeCl₃·7H₂O as an efficient catalyst for one-pot synthesis of β-amino ketones by three-component Mannich reaction, Chin. Chem. Lett. 21 (2010) 31-34.
9. [9]
  [9] V.A. Sukach, N.M. Golovach, V.V. Pirozhenko, et al., Convenient enantioselective synthesis of β-trifluoromethyl-b-aminoketones by organocatalytic asymmetric Mannich reaction of aryl trifluoromethyl ketimines with acetone, Tetrahedron 19 (2008) 761-764.
10. [10]
  [10] H. Wu, X.M. Chen, Y. Wan, et al., Stereoselective Mannich reactions catalyzed by Tröger's base derivatives in aqueous media, Tetrahedron Lett. 50 (2009) 1062-1065.
11. [11]
  [11] M.A. Bigdeli, F. Nemati, G.H. Mahdavinia, HClO₄-SiO₂ catalyzed stereoselective synthesis of β-amino ketones via a direct Mannich-type reaction, Tetrahedron Lett. 48 (2007) 6801-6804.
12. [12]
  [12] P. Phukan, D. Kataki, P. Chakraborty, Direct synthesis of Cbz-protected b-amino ketones by iodine-catalyzed three-component condensation of aldehydes, ketones and benzyl carbamate, Tetrahedron Lett. 47 (2006) 5523-5525.
13. [13]
  [13] Y.S. Wu, J. Cai, Z.Y. Hu, G.X. Lin, A new class of metal-free catalysts for direct diastereo-and regioselective Mannich reactions in aqueous media, Tetrahedron Lett. 45 (2004) 8949-8952.
14. [14]
  [14] Y.Y. Yang, W.G. Shou, Y.G. Wang, Synthesis of β-amino carbonyl compounds via a Zn(OTf)₂-catalyzed cascade reaction of anilines with aromatic aldehydes and carbonyl compounds, Tetrahedron 62 (2006) 10079-10086.
15. [15]
  [15] T.P. Loh, S.B.K.W. Liung, K.L. Tan, L.L. Wei, Three component synthesis of β-amino carbonyl compounds using indium trichloride-catalyzed one-pot Mannich-type reaction in water, Tetrahedron 56 (2000) 3227-3237.
16. [16]
  [16] U.S. Rai, A.M. Isloor, P. Shetty, et al., Synthesis and biological evaluation of aminoketones, Eur. J. Med. Chem. 45 (2010) 6090-6094.
17. [17]
  [17] R.I. Kureshy, S. Agrawal, S. Saravanan, et al., Direct Mannich reaction mediated by Fe(Cp)₂PF₆ under solvent-free conditions, Tetrahedron Lett. 51 (2010) 489-494.
18. [18]
  [18] C. Mukhopadhyay, A. Datta, R.J. Butcher, Highly efficient one-pot, three-component Mannich reaction catalysed by boric acid and glycerol in water with major‘syn’diastereoselectivity, Tetrahedron Lett. 50 (2009) 4246-4250.
19. [19]
  [19] M. Kidwai, N.K. Mishra, V. Bansal, et al., Novel one-pot Cu-nanoparticles-catalyzed Mannich reaction, Tetrahedron Lett. 50 (2009) 1355-1358.
20. [20]
  [20] C.T. Chang, B.S. Liao, S.T. Liu, Mannich-type reactions in a colloidal solution formed by sodium tetrakis(3,5-trifluoromethylphenyl)borate as a catalyst in water, Tetrahedron Lett. 47 (2006) 9257-9259.
21. [21]
  [21] M. Zahouily, Y. Abrouki, A. Rayadh, et al., Fluorapatite: efficient catalyst for the Michael addition, Tetrahedron Lett. 44 (2003) 2463-2465.
22. [22]
  [22] C.B. Yue, T.F. Yi, C.B. Zhu, G. Liu, Mannich reaction catalyzed by a novel catalyst under solvent-free conditions, J. Ind. Eng. Chem. 15 (2009) 653-656.
23. [23]
  [23] N. Saadatjoo, M. Golshekan, S. Shariati, et al., Ultrasound-assisted synthesis of bamino ketones via a Mannich reaction catalyzed by Fe₃O₄ magnetite nanoparticles as an efficient, recyclable and heterogeneous catalyst, Arab. J. Chem. (2012), http://dx.doi.org/10.1016/j.arabjc.2012.11.018.
24. [24]
  [24] G.P. Lu, C. Cai, Mannich reactions catalyzed by perchloric acid in Triton X10 aqueous micelles, Catal. Commun. 11 (2010) 745-748.
25. [25]
  [25] R.K. Sharma, D. Rawat, G. Gaba, Inorganic-organic hybrid silica based tin(Ⅱ) catalyst: synthesis, characterization and application in one-pot three-component Mannich reaction, Catal. Commun. 19 (2012) 31-36.
26. [26]
  [26] M. Wu, H. Jing, T. Chang, Synthesis of b-amino carbonyl compounds via a Mannich reaction catalyzed by SalenZn complex, Catal. Commun. 8 (2007) 2217-2221.
27. [27]
  [27] L. Wang, J. Han, J. Sheng, et al., Rare earth perfluorooctanoate [RE(PFO)₃] catalyzed one-pot Mannich reaction: three component synthesis of b-amino carbonyl compounds, Catal. Commun. 6 (2005) 201-204.
28. [28]
  [28] P.A. Grieco (Ed.), Organic Synthesis in Water, 1st ed., Blackie, London, 1998.
29. [29]
  [29] K. Ramesh, K. Karnakar, G. Satish, Y.V.D. Nageswar, Novel and efficient supramolecular synthesis of pyrroles in the presence of b-cyclodextrin in water, Chin. Chem. Lett. 23 (2012) 1331-1334.
30. [30]
  [30] M. Kidwai, D. Bhatnagar, N.K. Mishra, V. Bansal, CAN catalyzed synthesis of bamino carbonyl compounds via Mannich reaction in PEG, Catal. Commun. 9 (2008) 2547-2549.
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沈阳化工大学材料科学与工程学院沈阳 110142