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      一種1,2,4-三嗪-香豆素型化合物及其制法和用圖_3

      文檔序號:9837259閱讀:來源:國知局
      的制備 收率 65 ο/ο。1!! I、mk、d6-UMbu, 4υυ ivmz; 〇:
      w丄hj, ^.t>y1H), 3.84 (s, 6H), 4.12 (m, 3H), 5.61 (s, 1H), 6.36 (d, 1H), 6.82 (dd, 1H), 6.91 (d, 1H), 7.08 (m, 4H), 7.58 (m, 4H) , 7.67 (d, 1H), 7.88 (d, 1H); EIMS m/z = 544 [M+]。
      [0038] 實施例二十七:7-(3-( (5,6-二(2-乙基苯基)-1,2,4-三嗪-3-基)硫代)-2-羥基丙 氧基)-2H-苯并吡喃-2-酮(27)的制備
      收率 60 %</Η MMR (d6-DMS0,400 ΜΗζ) δ: 1.35 (t, 6H), 2.61 (q, 4H), 3.40 (dd, 1H), 3.59 (dd, 1H), 4.15 (m, 3H), 5.59 (s, 1H), 6.36 (d, 1H), 6.79 (dd, 1H), 6.90 (d, 1H), 7.36 (m, 6H), 7.60 (d, 1H), 7.68 (m, 2H), 7.79 (d, 1H); EIMS m/z = 540 [M+]〇
      [0039] 實施例二十八:7-(3-((5,6-二(3-乙基苯基)-1,2,4-三嗪-3-基)硫代)-2-羥基丙 氧基)-2H-苯并吡喃-2-酮(28 )的制備 V
      收率 84 %。咕 MMR (d6-DMS0,400 ΜΗζ) δ: 1.28 (t, 6H), 2.58 (q, 4H), 3.42 (dd, 1H), 3.57 (dd, 1H), 4.13 (m, 3H), 5.58 (s, 1H), 6.39 (d, 1H), 6.75 (dd, 1H), 6.88 (d, 1H), 7.28 (m, 2H), 7.34 (m, 2H), 7.48 (m, 2H), 7.64 (d, 1H), 7.67 (m, 2H), 7.77 (d, 1H); EIMS m/z = 540 [M+]〇
      [0040] 實施例二十九:7-(3-( (5,6-二(4-乙基苯基)-1,2,4-三嗪-3-基)硫代)-2-羥基丙 氧基)-2H-苯并吡喃-2-酮(29 )的制備 i
      收率 66 %</Η MMR (d6-DMS0, 400 MHz) δ: 1.26 (t, 6H), 2.59 (q, 4H), 3.44 (dd, 1H), 3.56 (dd, 1H), 4.17 (m, 3H), 5.56 (s, 1H), 6.41 (d, 1H), 6.74 (dd, 1H), 6.87 (d, 1H), 7.38 (m, 4H), 7.66 (d, 1H), 7.72 (m, 4H), 7.79 (d, 1H); EIMS m/z = 540 [M+]〇
      [0041 ] 實施例三十:7-(3-( (5,6-二(2-乙氧基苯基)-1,2,4-三嗪-3-基)硫代)-2-羥基丙 氧基)-2H-苯并吡喃-2-酮(30 )的制備
      收率 81 %</Η NMR (d6-DMS0,400 ΜΗζ) δ: 1.36 (t, 6H), 3.43 (dd, 1H), 3.57 (dd, 1H), 4.17 (m, 3H), 4.67 (q, 4H), 5.67 (s, 1H), 6.39 (d, 1H), 6.83 (dd, 1H), 6.86 (d, 1H), 7.09 (m, 2H), 7.13 (m, 2H), 7.35 (m, 2H), 7.61 (d, 1H), 7.85 (m, 2H), 7.89 (d, 1H); EIMS m/z = 572 [M+]〇
      [0042] 實施例三^^一:7-(3-((5,6-二(3-乙氧基苯基)-1,2,4-三嗪-3-基)硫代)-2-羥基 丙氧基)-2H-苯并吡喃-2-酮(31)的制備
      收率 77 %</Η NMR (d6-DMS0,400 ΜΗζ) δ: 1.34 (t,6H),3.44 (dd,1H),3.52 (dd, 1H), 4.11 (q, 4H), 4.15 (m, 3H), 5.62 (s, 1H), 6.35 (d, 1H), 6.77 (dd, 1H), 6.82 (d, 1H), 6.99 (m, 2H), 7.33 (m, 2H), 7.39 (m, 2H), 7.45 (m, 2H), 7.64 (d, 1H), 7.81 (d, 1H); EIMS m/z = 572 [M+]〇
      [0043] 實施例三十二:7-(3-((5,6-二(4-乙氧基苯基)-1,2,4-三嗪-3-基)硫代)-2-羥基 丙氧基)-2H-苯并吡喃-2-酮(32)的制備
      收率 75 %</Η NMR (d6-DMS0,400 ΜΗζ) δ: 1.31 (t,6H),3.43 (dd, 1H),3.56 (dd, 1H), 4.12 (q, 4H), 4.16 (m, 3H), 5.64 (s, 1H), 6.37 (d, 1H), 6.70 (dd, 1H), 6.84 (d, 1H), 7.13 (m, 4H), 7.59 (m, 4H), 7.67 (d, 1H), 7.83 (d, 1H); EIMS m/z = 572 [M+]〇
      [0044] 實施例三十三:7-( 3-( (5,6-二(2-羥基苯基)-1,2,4-三嗪-3-基)硫代)-2-羥基丙 氧基)-2H-苯并吡喃-2-酮(33)的制備
      收率 74 %</H NMR (d6-DMS0,400 ΜΗζ) δ: 3.44 (dd, 1H),3.62 (dd, 1H),4.18 (m, 3H), 5.42 (s, 2H), 5.66 (s, 1H), 6.35 (d, 1H), 6.83 (dd, 1H), 6.91 (d, 1H), 7.05 (m, 2H), 7.15 (m, 2H), 7.29 (m, 2H), 7.60 (d, 1H), 7.78 (m, 2H), 7.90 (d, 1H); EIMS m/z = 516 [M+]〇
      [0045] 實施例三十四:7-(3-( (5,6-二(3-羥基苯基)-1,2,4-三嗪-3-基)硫代)-2-羥基丙 氧基)-2H-苯并吡喃-2-酮(34)的制備
      收率 64 %</H NMR (d6-DMSO,400 MHz) δ: 3.41 (dd,1H),3.65 (dd,1H),4.14 (m, 3H), 5.39 (s, 2H), 5.60 (s, 1H), 6.39 (d, 1H), 6.80 (dd, 1H), 6.86 (d, 1H), 7.01 (m, 2H), 7.32 (m, 2H), 7.39 (m, 2H), 7.46 (m, 2H),7.61 (d, 1H), 7.92 (d, 1H); EIMS m/z = 516 [M+]〇
      [0046] 實施例三十五:7-( 3-( (5,6-二(4-羥基苯基)-1,2,4-三嗪-3-基)硫代)-2-羥基丙 氧基)-2H-苯并吡喃-2-酮(35)的制備
      收率 68 NMR (d6-DMS0,400 ΜΗζ) δ: 3.40 (dd,1H),3.62 (dd,1H),4.13 (m, 3H), 5.37 (s, 2H), 5.62 (s, 1H), 6.41 (d, 1H), 6.76 (dd, 1H), 6.89 (d, 1H), 6.91 (m, 4H), 7.56 (m, 4H), 7.63 (d, 1H), 7.95 (d, 1H); EIMS m/z = 516
      [M+]。
      [0047] 實施例三十六:7-( 3-( (5,6-二(2,3-二氟苯基)-1,2,4-三嗪-3-基)硫代)-2-羥基 丙氧基)-2H-苯并吡喃-2-酮(36)的制備
      收率 61 %</H NMR (d6-DMS0,400 ΜΗζ) δ: 3.47 (dd,1H),3.60 (dd,1H),4.19 (m, 3H), 5.67 (s, 1H), 6.39 (d, 1H), 6.82 (dd, 1H), 6.92 (d, 1H), 7.20 (m, 2H), 7.32 (m, 2H), 7.58 (m, 2H), 7.65 (d, 1H), 7.93 (d, 1H); EIMS m/z = 556
      [M+]〇
      [0048] 實施例三十七:7-( 3-( (5,6-二(2,3-二氯苯基)-1,2,4-三嗪-3-基)硫代)-2-羥基 丙氧基)-2H-苯并吡喃-2-酮(37)的制備
      收率 70 %</H NMR (d6-DMSO,400 MHz) δ: 3.45 (dd,1H),3.63 (dd,1H),4.10 (m, 3H), 5.65 (s, 1H), 6.41 (d, 1H), 6.80 (dd, 1H), 6.95 (d, 1H), 7.38 (m, 2H), 7.62 (m, 2H), 7.70 (d, 1H), 7.80 (m, 2H), 7.95 (d, 1H); EIMS m/z = 622
      [M+]〇
      [0049] 實施例三十八:7-( 3-( (5,6-二(2,3-二溴苯基)-1,2,4-三嗪-3-基)硫代)-2-羥基 丙氧基)-2H-苯并吡喃-2-酮(38)的制備
      收率 65 NMR (d6-DMS0,400 ΜΗζ) δ: 3.42 (dd,1H),3.66 (dd,1H),4.11 (m, 3H), 5.67 (s, 1H), 6.43 (d, 1H), 6.82 (dd, 1H), 6.97 (d, 1H), 7.35 (m, 2H), 7.68 (m, 2H), 7.65 (d, 1H), 7.68 (m, 2H), 7.93 (d, 1H); EIMS m/z = 800
      [M+]。
      [0050] 實施例三十九:7-(3-( (5,6-二(2,3-二硝基苯基)-1,2,4-三嗪-3-基)硫代)-2-羥 基丙氧基)-2H-苯并吡喃-2-酮(39)的制備
      收率 68 %</H NMR (d6-DMS0,400 ΜΗζ) δ: 3.44 (dd,1H),3.63 (dd,1H),4.11 (m, 3H), 5.65 (s, 1H), 6.33 (d, 1H), 6.80 (dd, 1H), 6.88 (d, 1H), 7.66 (d, 1H), 7.69 (m, 2H), 7.73(m, 2H), 7.88 (m, 2H), 7.97 (d, 1H); EIMS m/z = 664 [M + ]〇
      [0051] 實施例四十:7-(3-( (5,6-二(2,4-二氟苯基)-1,2,4-三嗪-3-基)硫代)-2-羥基丙 氧基)-2H-苯并吡喃-2-酮(40 )的制備
      收率 69 %</H NMR (d6-DMSO,400 MHz) δ: 3.40 (dd,1H),3.61 (dd,1H),4.13 (m, 3H), 5.66 (s, 1H), 6.37 (d, 1H), 6.69 (d, 2H), 6.78 (dd, 1H), 6.86 (d, 1H), 7.18 (m, 2H), 7.69 (d, 1H), 7.78 (d, 2H), 7.87 (d, 1H); EIMS m/z = 556 [M+]〇
      [0052] 實施例四 ^^一: 7-( 3-( (5,6-二(2,4-二氯苯基)-1,2,4-三嗪-3-基)硫代)-2-羥基 丙氧基)-2H-苯并卩喻-5·-Β耐41彳的擊丨I客
      收率 74 0/00? Mvm U6-uivibu, 4υυ ivmz; 〇: :?.^?:?〈αα,丄hj , J.b4〈ctd, 1H), 4.17 (m, 3H), 5.69 (s, 1H), 6.35 (d, 1H), 6.70 (dd, 1H), 6.88 (d, 1H), 7.48 (m, 2H), 7
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