OALib Journal期刊
ISSN: 2333-9721
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铜催化异噁唑还原开环清洁高效合成1-氨基-2-乙酰基蒽醌
DOI: 10.1016/S1872-2067(12)60743-8, PP. 319-323
Keywords: 铜催化剂,还原开环,1-氨基-2-乙酰基蒽醌,3-甲基蒽醌-[1,2-c]-异噁唑,清洁合成
Abstract:
?以水为反应介质,水合肼为还原剂,研究了痕量铜催化3-甲基蒽醌-[1,2-c]-异噁唑还原开环反应以清洁高效合成1-氨基-2-乙酰基蒽醌,考察了不同种类过渡金属硝酸盐的催化性能,发现Cu(NO3)2性能最好.加入2.6%的催化剂和1.3倍的水合肼,在室温反应2h,底物转化率和目标产物选择性分别可达到97.2%和95%,TON达到38.产品结构经氢核磁谱和质谱得以确证,主要副产为羟基取代的1-氨基-2-乙酰基蒽醌.此外,提出了铜催化3-甲基蒽醌-[1,2-c]-异噁唑还原开环反应合成1-氨基-2-乙酰基蒽醌的可能反应机理.
References
[1] | Zhang X S, Song X X, Li H, Zhang S L, Chen X B, Yu X H, Wang W. Angew Chem Int Ed, 2012, 51: 7282
|
[2] | Zhao Z K, Li R Z, Li Y, Chen G T. CN Patent 102603547A. 2012
|
[3] | Akiba K, Kashiwagi K, Ohyama Y, Yamamoto Y, Ohkata K. J Am Chem Soc, 1985, 107: 2721
|
[4] | Konwar D, Boruah R C, Sandhu J S. Chem Ind, 1989, 6: 191
|
[5] | Auricchio S, Bini A, Pastomerlo E, Truscello A M. Tetrahedron, 1997, 53: 10911
|
[6] | Kijima M, Nambu Y, Endo T. J Org Chem, 1985, 50: 1140
|
[7] | Fan X S, Zhang Y M. Tetrahedron Lett, 2002, 43: 7001
|
[8] | Konwar D, Boruah R C, Sandhu J S, Baruah J N. Synth Commun, 1984, 14: 1053
|
[9] | Wilke K. US Patent 1830152. 1931
|
[10] | Vasilevsky S F, Gornostaev L M, Stepanov A A, Arnold E V, Alabugin I V. Tetrahedron Lett, 2007, 48: 1867
|
[11] | Sharma U, Verma P K, Kumar N, Kumar V, Bala M, Singh B. Chem Eur J, 2011, 17: 5903
|
[12] | Marsh B J, Heath E L, Carbery D R. Chem Commun, 2011, 47: 280
|
[13] | Kinjo R, Donnadieu B, Bertrand G. Angew Chem Int Ed, 2011, 50: 5560
|
[14] | Britvin S N, Lotnyk A, Kienle L, Krivovihev S V, Depmeier W. J Am Chem Soc, 2011, 133: 9516
|
[15] | Zhao Z K, Li R Z, Li Y. ScienceJet, 2013, 2: 41
|
[16] | Zhang X H, Wang L Y, Zhan Y H, Fu Y L, Zhai G H, Wen Z Y. J Mol Struct, 2011, 994: 371
|
[17] | Li Y T, Chen C L, Hsu Y Y, Hsu H C, Chi Y, Chen B S, Liu W H, Lai C H, Lin T Y, Chou P T. Tetrahedron, 2010, 66: 4223
|
[18] | Amino M S, Mahmoud A A, Badr S K, Gouda A S. J Surf Det, 2012, 15: 179
|
[19] | Velcicky J, Soicke A, Steiner R, Schmalz H G. J Am Chem Soc, 2011, 133: 6948
|
[20] | Zolfigol M A, Salehi P, Shiri M, Rastegar T F, Ghaderi A. J Iran Chem Soc, 2008, 5: 490
|
[21] | Krasavin M, Busel A, Parchinsky V. Tetrahedron Lett, 2009, 50: 5945
|
[22] | Vergelli C, Giovannoni M P, Pieretti S, Di Giannuario A, Dal Piaz V, Biagini P, Biancalani C, Graziano A, Cesari N. Bioorg Med Chem, 2007, 15: 5563
|
[23] | Walker G N. J Org Chem, 1962, 27: 1929
|
[24] | Oster T A, Harris T M. J Org Chem, 1983, 48: 4307
|
[25] | Caplan J F, Zheng R J, Blanchard J S, Vederas J C. Org Lett, 2000, 2: 3857
|
[26] | Charest M G, Siegel D R, Myers A G. J Am Chem Soc, 2005, 127: 8292
|
[27] | Mohatt J L, Hu L H, Finneran K T, Strathmann T J. Environ Sci Technol, 2011, 45: 4793
|
[28] | Angibaud P R, Venet M G, Filliers W, Broeckx R, Ligny Y A, Muller P, Poncelet V S, End D W. Eur J Org Chem, 2004: 479
|
[29] | Natale N R. Tetrahedron Lett, 1982, 23: 5009
|
[30] | Olah G A, Narang S C, Tetrahedron, 1982, 38: 2225
|
[31] | Epple G, Flohr H. DE Patent 2912570A1. 1980
|
[32] | Wilke K. US Patent 1830153. 1931
|
[33] | Lamani M, Guralamata R S, Prabhu K R. Chem Commun, 2012, 48: 6583
|
[34] | Gao Y J, Ma D, Wang C L, Guan J, Bao X H. Chem Commun, 2011, 47: 2432
|
[35] | Shil A K, Sharma D, Guha N R, Das P. Tetrahedron Lett, 2012, 53: 4858
|
[36] | Daff T D, de Leeuw N H. Chem Mater, 2011, 23: 2718
|
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