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Synlett 2013; 24(19): 2596-2600
DOI: 10.1055/s-0033-1339898
DOI: 10.1055/s-0033-1339898
letter
Study on the Influence of a Sustainable Medium for the Design of Multistep Processes: Three-Component Synthesis of 2-Nitroamines
Weitere Informationen
Publikationsverlauf
Received: 23. Juli 2013
Accepted after revision: 05. September 2013
Publikationsdatum:
16. Oktober 2013 (online)

Abstract
An environmentally benign method was developed for the three-component, one-pot synthesis of 2-nitroamines by heating a solution of an aldehyde, an aromatic amine, and a nitroalkane in 20% water–methanol at 60 °C for five hours in the absence of a catalyst.
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References
- 1a Ugi I. Pure Appl. Chem. 2001; 73: 187
- 1b Ugi I, Heck S. Comb. Chem. High Throughput Screening 2001; 4: 1
- 1c Dömling A, Ugi I. Angew. Chem. Int. Ed. 2000; 39: 3168
- 2 von Wangelin AJ, Neumann H, Gördes D, Klaus S, Strübing D, Beller M. Chem. Eur. J. 2003; 9: 4286
- 3a Henderson RK, Jimènez-González C, Constable DJ. C, Alston SR, Inglis GG. A, Fisher G, Sherwood J, Binksa SP, Curzons AD. Green Chem. 2011; 13: 854
- 3b Strauss CR. Aust. J. Chem. 1999; 52: 83
- 4a Bigi F, Chesini L, Maggi R, Sartori G. J. Org. Chem. 1999; 64: 1033
- 4b Sartori G, Bigi F, Maggi R, Mazzacani A, Oppici G. Eur. J. Org. Chem. 2001; 2513
- 4c Maggi R, Bigi F, Carloni S, Mazzacani A, Sartori G. Green Chem. 2001; 3: 173
- 4d Soldi L, Ferstl W, Loebbecke S, Maggi R, Malmassari C, Sartori G, Yadab S. J. Catal. 2008; 258: 289
- 5 Ballini R, Barboni L, Fringuelli F, Palmieri A, Pizzo F, Vaccaro L. Green Chem. 2007; 9: 823
- 6a Baer HH, Urbas L In The Chemistry of the Nitro and Nitroso Groups . Patai S. Interscience; New York: 1970. Part 2 117
- 6b Nishiwaki N, Knudsen KR, Gothelf KV, Jørgensen KA. Angew. Chem. Int. Ed. 2001; 40: 2992
- 6c Qian C, Gao F, Chen R. Tetrahedron Lett. 2001; 42: 4673
- 6d Singh A, Yoder RA, Shen B, Johnston JN. J. Am. Chem. Soc. 2007; 129: 3466
- 6e Noble A, Anderson JC. Chem. Rev. 2013; 113: 2887
- 7a Stacy GW, Morath RJ. J. Am. Chem. Soc. 1952; 74: 3885
- 7b Adams H, Anderson JC, Peace S, Pennell AM. K. J. Org. Chem. 1998; 63: 9932
- 8 Anderson JC, Peace S, Pih S. Synlett 2000; 850
- 9 Kundu D, Debnath RK, Majee A, Hajra A. Tetrahedron Lett. 2009; 50: 6998
- 10 Marqués-López E, Merino P, Tejero T, Herrera RP. Eur. J. Org. Chem. 2009; 2401
- 11 Tanaka K, Shiraishi R. Green Chem. 2000; 2: 272
- 12 Manabe K, Iimura S, Sun X.-M, Kobayashi S. J. Am. Chem. Soc. 2002; 124: 11971
- 13a Klijn JE, Engberts JB. F. N. Nature 2005; 435: 746
- 13b Narayan S, Muldoon J, Finn MG, Fokin VV, Kolb HC, Sharpless KB. Angew. Chem. Int. Ed. 2005; 44: 3275
- 14a Grieco PA, Yoshida K, Garner P. J. Org. Chem. 1983; 48: 3137
- 14b Breslow R, Maitra U. Tetrahedron Lett. 1984; 25: 1239
- 15a Li C.-J. Chem. Rev. 1999; 93: 2023
- 15b Li C.-J, Chen L. Chem. Soc. Rev. 2006; 35: 68
- 15c Lubineau A, Augé J, Queneau Y. Synthesis 1994; 741
- 15d Bonollo S, Lanari D, Vaccaro L. Eur. J. Org. Chem. 2011; 2587
- 16 Lindström UM, Andersson F. Angew. Chem. Int. Ed. 2006; 45: 548 ; and references cited therein
- 17 Jung Y, Marcus RA. J. Am. Chem. Soc. 2007; 129: 5492
- 18 Breslow R. Acc. Chem. Res. 1991; 24: 159
- 19 A method for synthesizing imines from amines and aldehydes in aqueous suspension has been previously reported; see ref. 11. However, this solvent-free approach gave a poor yield (~20%) of the model product 5aaa when applied to the present three-component reaction described in Scheme 1.
- 20a Dickerson TJ, Janda KD. J. Am. Chem. Soc. 2002; 124: 3220
- 20b Hayashi Y. Angew. Chem. Int. Ed. 2006; 45: 8103
- 20c Brogan AP, Dickerson TJ, Janda KD. Angew. Chem. Int. Ed. 2006; 45: 8100
- 20d Huang J, Zhang X, Armstrong DW. Angew. Chem. Int. Ed. 2007; 46: 9073
- 21 PhCHO (1a; 1 mmol) and PhNH2 (2a; 1 mmol) were stirred in H2O (5 mL) or 1 M aq LiCl (5 mL) at 60 °C for 10 min to give imine 3aa in 75 and 78% yield, respectively. In a second experiment, PhCHO (1a; 1 mmol), PhNH2 (2a; 1 mmol), and MeNO2 (4a; 10 mmol) were stirred in H2O (5 mL) or 1 M aq LiCl (5 mL) at 60 °C for 30 min to give nitro amine 5aaa in 37 and 39% yield, respectively.
- 22a Henry L. C. R. Acad. Sci., Ser. C 1895; 126
- 22b Henry L. Bull. Soc. Chim. Fr. 1895; 13: 999
- 22c Rosini G In Comprehensive Organic Synthesis II . Vol. 2. Trost BM, Fleming I. Pergamon; Oxford: 1991: 321
- 23a Ziyaei-Halimehjani A, Saidi MR. Tetrahedron Lett. 2008; 49: 1244
- 23b Petersen S, Mitrowsky A. GB 771566, 1957
- 23c Mahasneh AS. Abhath Al-Yarmouk, Basic Sci. Eng. 2004; 13: 79
- 23d Shoemaker GL, Keown RW. Trans. Ky. Acad. Sci. 1955; 16: 85
- 23e Ai X, Wang X, Liu J.-m, Ge Z.-m, Cheng Z.-m, Li R.-t. Tetrahedron 2010; 66: 5373
- 23f Leonard NJ, Leubner GW, Burk EH. Jr. J. Org. Chem. 1950; 15: 979
All 2-nitroamines 5 synthesized are known compounds, see: