2-氨基芴类化合物是重要有机合成中间体,广泛用于合成农药、医药、精细化工中间体、燃料、光电材料和农用化学品等;用作有机合成中间体,用于有机合成。
医药; 农药; 精细化工中间体; 燃料; 光电材料; 农用化学品
合成路线 1
- 步骤: 将硝基芳烃(1mmol)、SS-Pd(2mol/l Pd)和硼氢化钠(3mmol)的混合物置于25ml圆底烧瓶中,在0℃下搅拌条件下通过注射器加入3ml MeOH:H₂O(3:7),10分钟后加热至50℃,TLC监测反应进程,完成后用乙酸乙酯萃取,无水Na₂SO₄干燥,蒸发有机层后硅胶柱色谱分离得到目标胺。
- 条件: 以硼氢化钠为还原剂,甲醇-水(3:7)为溶剂,反应温度0-50℃,反应时间2小时。
- 产率: 99%
- 参考文献: [1] Analytical Chemistry, 1988, vol. 60, # 3, p. 194-199;[2] Tetrahedron Letters, 2012, vol. 53, # 36, p. 4858-4861;[3] Chemical Communications, 2013, vol. 49, # 86, p. 10088-10090;[4] ChemSusChem, 2017, vol. 10, # 15, p. 3035-3039;[5] Applied Organometallic Chemistry, 2018, vol. 32, # 1;[6] Patent: WO2018/114777, 2018, A1(Page/Page column 31-32);[7] ChemSusChem, 2018, vol. 11, # 18, p. 3131-3138;[8] Catalysis Communications, 2015, vol. 67, p. 64-67;[9] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 1749-1757;[10] Advanced Synthesis and Catalysis, 2012, vol. 354, # 2-3, p. 321-327;[11] Turkish Journal of Chemistry, 2017, vol. 41, # 5, p. 784-792;[12] Tetrahedron Letters, 1980, vol. 21, # 27, p. 2603-2604;[13] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1988, vol. 24, p. 87-92;[14] Khimiya Geterotsiklicheskikh Soedinenii, 1988, vol. 24, # 1, p. 104-109;[15] Tetrahedron Letters, 2014, vol. 55, # 18, p. 2912-2916;[16] Tetrahedron Letters, 2000, vol. 41, # 30, p. 5603-5606;[17] ChemCatChem, 2017, vol. 9, # 6, p. 1128-1134;[18] Synthetic Communications, 2000, vol. 30, # 20, p. 3745-3754;[19] Heterocycles, 2004, vol. 63, # 2, p. 283-296;[20] Patent: US6362200, 2002, B1(Example 2);[21] Catalysis Letters, 2014, vol. 144, # 7, p. 1258-1267;[22] European Journal of Organic Chemistry, 2016, vol. 2016, # 20, p. 3307-3309;[23] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 4, p. 984-988;[24] Patent: US2011/77394, 2011, A1(Page/Page column 15);[25] Chemistry - A European Journal, 2016, vol. 22, # 32, p. 11291-11302;[26] Journal of Organometallic Chemistry, 1981, vol. 219, # 1, p. 125-127;[27] European Journal of Organic Chemistry, 2011, # 4, p. 672-675;[28] Journal of Nanoscience and Nanotechnology, 2018, vol. 18, # 11, p. 7873-7881;[29] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2018, vol. 189, p. 22-31;[30] New Journal of Chemistry, 2018, vol. 42, # 2, p. 1373-1378;[31] Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 2, p. 776-779;[32] Chemische Berichte, 1901, vol. 34, p. 1759;[33] Organic Syntheses, 1960, vol. 40, p. 5;[34] Journal of the American Chemical Society, 1947, vol. 69, p. 712;[35] Journal of the American Chemical Society, 1949, vol. 71, p. 1893 Anm.2;[36] Canadian Journal of Chemistry, 1957, vol. 35, p. 1084,1085;[37] Zhurnal Obshchei Khimii, 1957, vol. 27, p. 234,237;engl.Ausg.S.261,264;[38] Journal of Organic Chemistry, 1958, vol. 23, p. 680,683;[39] Journal of the Chemical Society, 1957, p. 207;[40] Journal of the Chemical Society, 1955, p. 2686,2688;[41] Chemische Berichte, 1884, vol. 17, p. 107;[42] Journal of the Chemical Society, 1908, vol. 93, p. 1763;[43] Organic Syntheses, 1933, vol. 13, p. 75;[44] Coll.Vol., 1943, vol. II, p. 448;[45] Canadian Journal of Chemistry, 1957, vol. 35, p. 1084,1085;[46] Zhurnal Obshchei Khimii, 1957, vol. 27, p. 234,237;engl.Ausg.S.261,264;[47] Journal of Organic Chemistry, 1958, vol. 23, p. 680,683;[48] Molecular Crystals and Liquid Crystals (1969-1991), 1986, vol. 133, p. 111-124;[49] Chemical Research in Toxicology, 2000, vol. 13, # 8, p. 793-800;[50] Chemical Research in Toxicology, 1998, vol. 11, # 11, p. 1361-1367;[51] Chemical Research in Toxicology, 2002, vol. 15, # 4, p. 536-544;[52] Bulletin de la Societe Chimique de France, 1927, vol. <4> 41, p. 69;[53] Chemical Communications, 2010, vol. 46, # 10, p. 1769-1771;[54] Advanced Synthesis and Catalysis, 2011, vol. 353, # 8, p. 1306-1316;[55] Chemistry - A European Journal, 2011, vol. 17, # 21, p. 5903-5907;[56] Chemical Communications, 2011, vol. 47, # 39, p. 10972-10974;[57] Chemical Communications, 2013, vol. 49, # 80, p. 9089-9091;[58] Synlett, 2015, vol. 26, # 3, p. 313-317;[59] ACS Catalysis, 2015, vol. 5, # 3, p. 1526-1529;[60] Chemical Communications, 2015, vol. 51, # 66, p. 13086-13089;[61] RSC Advances, 2015, vol. 5, # 105, p. 86529-86535;[62] Catalysis Science and Technology, 2016, vol. 6, # 12, p. 4473-4477;[63] Journal of Catalysis, 2017, vol. 351, p. 79-89;[64] Applied Catalysis A: General, 2018, vol. 559, p. 127-137;[65] Chemistry - A European Journal, 2018, vol. 24, # 70, p. 18682-18688
合成路线 2
- 步骤: 将2-硝基芴用锌粉还原。