一种含1,2,4-三唑硫酮希夫碱的喹唑啉酮类化合物的合成方法及应用_2

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ζ) δ: 5.42 (s, 2Η), 7.17 (t, J = 7.45 Hz, 1H), 7.28 (t, J = 7.45 Hz, 1H), 7.53 (d, J = 8.00 Hz, 1H), 7.58 (t, J = 8.00 Hz, 1H), 7.70 (d, J = 8.00 Hz, 1H), 7.87 (t, J = 7.50 Hz, 1H), 8.11-8.17 (m, 3H), 8.47 (s, 1H), 9.79 (s, 1H), 12.07 (s, 1H), 13.82 (s, 1H); 13C 匪R (DMS〇-d6, 125 MHz) δ: 41.30,110.30,112.90,121.92, 122.14, 122.64, 123.86, 124.65, 126.65, 127.86, 127.89, 135.25, 136.37, 137.93, 147.25, 148.40, 148.47, 160.52, 161.87, 162.53. IR (KBr, cm-1) v: 3258, 3064, 2930, 1695, 1616; Anal. Calcd for C20H15N7OS: C, 59.84; H, 3.77; N, 24.42. Found: C, 60.14; H, 4.10; N, 24.69. MS (ESI) m/z: 402.1 ([M+H]+), 424.1 ([M+Na]+). 实施例四:化合物3-( (4-( (3-甲氧基-4-羟基苄烯基)氨基)-5-硫酮-4,5-二氢-1H-1, 2,4-三唑-3-基)甲基)喹唑啉-4(3H)-酮的合成(化合物编号F4):
步骤(1)-(5)同实施例一步骤(1)-(5); 步骤(6)如实施例一步骤(6)方法和条件合成,区别在于以3-甲氧基-4-羟基苯甲醛为 原料,反应后提纯得白色固体,收率40.7%。!!!.?. >250 UH NMR (DMS〇-d6,500 ΜΗζ) δ: 3.87 (s, 3Η), 5.39 (s, 2H), 6.91 (d, J = 8.00 Hz, 1H), 7.28 (dd, Ji= 7.45 Hz, J2= 7.45 Hz, 1H), 7.46 (d, J = 2.50 Hz, 1H), 7.57 (t, J = 8.00 Hz, 1H), 7.69 (d, J = 8.00 Hz, 1H), 7.86 (t, J = 7.00 Hz, 1H), 8.14 (d, J = 7.00 Hz, 1H), 8.49 (s, 1H), 9.70 (s, 1H), 10.07 (s, 1H), 13.95 (s, 1H); 13C 匪R (DMS〇-d6, 125 MHz) δ: 41.47, 56.16, 110.39, 116.05, 121.91, 123.56, 125.57, 126.62, 127.80, 127.90, 135.27, 147.05, 148.33, 148.72, 148.76, 152.12, 160.52, 162.46, 164.69. IR (KBr, cm-1) v: 3444, 3067, 2922, 1684, 1617; Anal. Calcd for CigHieNeOsS: C, 55.87; H, 3.95; N, 20.58. Found: C, 55.98; H, 4.31; N, 20.77. MS (ESI) m/z: 409.1 ([M+H]+), 431.1 ([M+Na]+). 实施例五:化合物3-( (4-((萘-2-甲烯基)氨基)-5-硫酮-4,5-二氢-1H-1,2,4-三唑-3-基)甲基)喹唑啉-4( 3H)-酮的合成(化合物编号F5):
步骤(1)-(5)同实施例一步骤(1)-(5); 步骤(6)如实施例一步骤(6)方法和条件合成,区别在于以萘-2-甲醛为原料,反应后提 纯得到白色固体,收率36.2%。1114· >250°C;咕 NMR (DMS〇-d6, 500 ΜΗζ) δ: 5.48 (s, 2Η), 7.58 (t, J = 7.45 Hz, 1H), 7.63-7.72 (m, 3H), 7.86 (t, J = 7.00 Hz, 1H), 8.03 (d, J = 7.50 Hz, 1H), 8.07-8.10 (m, 3H), 8.17 (d, J = 7.50 Hz, 1H), 8.41 (s, 1H), 8.52 (s, 1H), 10.34 (s, 1H), 14.06 (s, 1H); 13C 匪R (DMS〇-d6, 125 MHz) δ: 41.25, 121.92, 122.90, 126.66, 127.73, 127.87, 127.94, 128.47, 129.02, 129.47, 129.52, 130.15, 133.00, 133.09, 135.29, 135.42, 147.59, 148.37, 148.57, 160.54, 162.56, 162.89. IR (KBr, cm-1) v: 3461, 3059, 2955, 1691, 1617; Anal. Calcd for C22H16N6OS: C, 64.06; H, 3.91; N, 20.38. Found: C, 64.23; H, 4.35; N, 20.65. MS (ESI) m/z: 413.1 ([M+H]+), 435.1 ([M+Na]+). 实施例六:化合物3-( (4-( (2-甲氧基苄烯基)氨基)-5-硫酮-4,5-二氢-1H-1,2,4-三 唑-3-基)甲基)喹唑啉-4(3H)-酮的合成(化合物编号F6):
步骤(1)-(5)同实施例一步骤(1)-(5); 步骤(6)如实施例一步骤(6)方法和条件合成,区别在于以邻甲氧基苯甲醛为原料,反 应完后提纯得到白色固体,收率55.9%。1114. 228-229 °C;咕 NMR (DMS〇-d6, 500 ΜΗζ) δ: 3.89 (s, 3H), 5.41 (s, 2H), 7.09 (t, J = 7.45 Hz, 1H), 7.20 (d, J = 8.00 Hz, 1H), 7.56-7.63 (m, 2H), 7.70 (d, J = 8.00 Hz, 1H), 7.86 (t, J = 8.00 Hz, 1H), 7.97 (d, J = 7.45 Hz, 1H), 8.15 (d, J = 8.00 Hz, 1H), 8.46 (s, 1H), 10.42 (s, 1H), 13.99 (s, 1H); 13C NMR (DMS〇-d6, 125 MHz) δ: 41.19, 56.58, 112.86, 120.53, 121.42, 121.89, 126.64, 127.01, 127.84, 127.92, 135.20, 135.27, 147.60, 148.35, 148.52, 158.49, 159.81, 160.50, 162.38. IR (KBr, cm-1) v: 3443, 3052, 2901, 1684, 1616; Anal. Calcd for Ci9Hi6N6〇2S: C, 58.15; H, 4.11; N, 21.42. Found: C, 58.46; H, 4.52; N, 21.76. MS (ESI) m/z: 393.2 ([M+H]+), 415.1 ([M+Na]+). 实施例七:化合物3-( (4-( (4-叔丁基苄烯基)氨基)-5-硫酮-4,5-二氢-1H-1,2,4-三 唑-3-基)甲基)喹唑啉-4(3H)-酮的合成(化合物编号F7):
步骤(1)-(5)同实施例一步骤(1)-(5); 步骤(6)如实施例一步骤(6)方法和条件合成,区别在于以对叔丁基苯甲醛为原料,反 应完成后得白色固体,收率:52.4%。1114· 245-247 °C;咕匪R (DMS〇-d6, 500 ΜΗζ) δ: 1.33 (s, 9H), 5.40 (s, 2H), 7.56-7.59 (m, 3H), 7.71 (d, J = 8.00 Hz, 1H), 7.82-7.88 (m, 3H), 8.15 (d, J = 7.45 Hz, 1H), 8.48(s, 1H), 10.00 (s, 1H), 14.01 (s, 1H); 13C 匪R (DMS〇-d6,125 MHz) δ: 31.37,35.46,41.16,121.89, 126.56, 126.64, 127.85, 127.92, 129.15, 129.77, 135.28, 147.38, 148.35, 148.54, 156.54, 160.51, 162.51, 163.82. IR (KBr, cm-1) v: 3461, 3065, 2958, 1681, 1617; Anal. Calcd for C22H22N6OS: C, 63.14; H, 5.30; N, 20.08. Found: C, 63.52; Η, 5.65; Ν, 20.19. MS (ESI) m/z: 419.2 ([M+H]+), 441.2 ([M+Na]+). 实施例八:化合物3-( (4-( (4-甲基苄烯基)氨基)-5-硫酮-4,5-二氢-1H-1,2,4-三唑-3-基)甲基)喹唑啉-4( 3H)-酮的合成(化合物编号F8):
步骤(1)-(5)同实施例一步骤(1)-(5); 步骤(6)如实施例一步骤(6)的方法和条件合成,区别在于以对甲基苯甲醛为原料,反 应完成后得白色固体,收率49.5%。1114. >250 °C;咕匪R (DMS〇-d6, 500 ΜΗζ) δ: 2.34 (s, 3H), 5.34 (s, 2H), 7.31 (d, J = 7.45 Hz, 2H), 7.51 (t, J = 7.45 Hz, 1H), 7.64 (d, J = 8.00 Hz, 1H), 7.72 (d, J = 8.00 Hz, 2H), 7.80 (t, J = 7.45 Hz, 1H), 8.08 (d, J = 7.45 Hz, 1H), 8.40 (s, 1H), 9.94 (s, 1H), 13.94 (s, 1H); 13C 匪R (DMS〇-d6, 125 MHz) δ: 21.82, 41.20, 121.89, 126.64, 127.85, 127.94, 129.25, 129.76, 130.31, 135.29, 143.77, 147.43, 148.34, 148.53, 160.50, 162.50, 163.70.1 R (KBr, cm-1) v: 3461, 3067, 2920, 1684, 1617; Anal. Calcd for CigHieNeOS: C, 60.62; H, 4.28; N, 22.33. Found: C, 60.88; H, 4.59; N, 22.56. MS (ESI) m/z: 377.1 ([M+H]+), 399.1 ([M+Na]+). 实施例九:化合物3-( (4-( (3-羟基-4-甲氧基苄烯基)氨基)-5-硫酮-4,5-二氢-1H-1, 2,4-三唑-3-基)甲基)喹唑啉-4(3H)-酮的合成(化合物编号F9):
步骤(1)-(5)同实施例一步骤(1)-(5); 步骤(6)如实施例一步骤(6)的方法和条件合成,区别在于以3-羟基-4-甲氧基苯甲醛 为原料,反应完成后得白色固体,收率46.2%。!!!.?. >250 °C;咕NMR (DMS〇-d6,500 MHz) δ: 3.87 (s, 3H), 5.37 (s, 2H), 7.08 (d, J = 8.00 Hz, 1H), 7.30 (dd, Ji= 2.50 Hz, J2= 2.50 Hz, 1H), 7.40 (d, J = 2.50 Hz, 1H), 7.58 (d, J = 8.00 Hz, 1H), 7.71 (d, J = 8.00 Hz, 1H), 7.87 (t, J = 8.00 Hz, 1H), 8.15 (d, J = 8.00 Hz, 1H), 8.47 (s, 1H), 9.52 (s, 1H), 9.75 (s, 1H), 13.95 (s, 1H); 13C NMR (DMSO-de, 125 MHz) δ: 41.10, 56.28, 112.39, 113.84, 121.89, 123.59, 124.99, 126.64, 127.86, 127.92, 135.28, 147.38, 147.56, 148.39, 148.51, 152.63, 160.47, 162.56, 164.54. IR (KBr, cm-1) v: 3397, 3068, 2931, 1683, 1608; Anal. Calcd for CigHieNeOsS: C, 55.87; H, 3.95; N, 20.58. Found: C, 60.13; H, 4.32; N, 20.71. MS (ESI) m/z: 409.1 ([M+H]+), 431.1 ([M+Na]+). 实施例十:化合物3-( (4-( (2-氯苄烯基)氨基)-5-硫酮-4,5-二氢-1H-1,2,4-三唑-3-基)甲基)喹唑啉-4(3H)-酮的合成(化合物编号F10):
步骤(1)-(5)同实施例一步骤(1)-(5); 步骤(6)如实施例一步骤(6)的方法和条件合成,区别在于以邻氯苯甲醛为原料,反应 完成后提纯得白色固体,收率58.9%。1114. >250 °C;咕 NMR (DMS〇-d6, 500 ΜΗζ) δ: 5.47 (s, 2H), 7.50-7.54 (m, 1H), 7.58 (t, J = 8.00 Hz, 1H), 7.63-7.66 (m, 2H), 7.71 (d, J = 8.00 Hz, 1H), 7.86 (t, J = 8.00 Hz, 1H), 8.16-8.18 (m, 2H), 8.48 (s, 1H), 10.92 (s, 1H), 14.08 (s, 1H); 13C 匪R (DMS〇-d6, 125 MHz) δ: 41.04, 121.90, 126.66, 127.86, 127.
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