一种喹喔啉衍生物的高效合成方法_2

文档序号:9742281阅读:来源:国知局
7.2Hz,3H,CH3CH2-),4.36(q,J = 7.2Hz,2H,CH3CH2-) ,7.54~7.55(m,3H,Ar-H) ,7.75~7.77(m,2H,Ar-H),7.95(dd,J = 8.9Hz,2.2Hz,lH,Ar-H),8.07(d,J = 8.9Hz,lH,Ar-H),8.41(d,J = 2.1Hz,lH,Ar-H);13C NMR (125MHz,CDC13)S13.75,62.27,124.58,128.55,128.73,128.85,129.86,130.63,130.92, 131.75,137.38,140.43,141.03,146.53,152.45,166.29.
[0041 ] 实施例5
[0042]
合物为黄色固体,产率72%,m.p.65~66°C.其合成方法同实施 例 1,结构数据表征为:4 NMR(500MHz,CDC13)δ 1 · 20(t,J = 7 · 1Hz,3H,CH3CH2_),4 · 36(q,J = 7.1Hz,2H,CH3CH2-),7.53~7.54(m,lH,Ar-H),7.76~7.77(m,lH,Ar-H),7.84~7.91(m,lH, Ar-H),8.21~8.26(m,lH,Ar-H);13CNMR(125MHz,CDCl 3)Sl3.75,62.41,128.58,128.65, 129.37,129.59,130.54,131.70,137.82,139.94,142.28,145.76,152.28,166.62.
[0043] 实施例6
[0044]
合物为黄色油状物,产率75% .其合成方法同实施例1,结构数据 表征为:4 Mffi(500MHz,CDCl3)Sl.22(t,J = 7.2Hz,3H,CH3CH2-),2.87(s,3H,CH3-),4.37 (q,J = 7.2Hz,2H,CH3CH2-),7.53~7.56(m,3H,Ar-H),7.72~7.73(m,2H,Ar-H),7.82~7.84 (m,2H,Ar-H),8.07~8.08(m,lH,Ar-H) ;13CNMR(126MHz,CDCl3)Sl67.02,150.70,145.14, 141.45,139.97,138.14,137.88,131.48,130.27,129.50,128.81,128.56,127.30,62.35, 17.10,13.78.
[0045] 实施例7
[0046]
合物为白色固体,产率80 %,m. p. 79~80°C .其合成方法同实施 例1,结构数据表征为匪R(500MHz,CDCl3)S8.40(d,J = 8.4Hz,lH,Ar-H),8.21(d,J = 7.3Hz,lH,Ar-H),7.87(dt,J=11.2,4.7Hz,3H,Ar-H),7.57~7.53(m,3H,Ar-H),4.40(q,J =7.1Hz,2H,CH3CH2-) ,1.23(t,J = 7.1Hz,3H,CH3CH2-) ;13C 匪R( 126MHz,CDC13)S166.44 (s),152.07(s),146.39(s),139.64(s),139.12(s),136.95(s),133.74(s),130.20(s), 129.68(t,J = 5.3Hz) ,128.95(d,J = 4.7Hz) ,128.70(s) ,128.30(s) ,128.06( s) ,124.44 (s),122.26(s),62.66(s),13.74(s).
[0047] 实施例8
[0048]
合物为黄色固体,产率71%,m. p.131~133°C.其合成方法同 实施例 1,结构数据表征为:4 NMR(500MHz,CDC13)δ8 · 00(dd,J = 8 · 0,2 · 7Hz,1H,Ar-H),7 · 87 ~7.82(m, 3H,Ar-H),7.56~7.53(m,3H,Ar-H),4.38(q,J=7.1Hz,2H,CH3CH2-),1.22(t,J =7·1Hz,3H,CH3CH2-); 13C NMR(126MHz,CDC13)S166· 19,163.16,161.12,151.77,151.75, 147.05,140.84,140.73,137.37,137.36,136.83,130.09,128.87,128.75,125.86,125.77, 125.71,125.48,112.91,112.74,62.70,13.74.
[0049] 实施例9
[0050]
化合物为白色固体,产率81%,m.ρ.115~116°C.其合成方法同实 施例1,结构数据表征为:1!1匪1?(5001!^,0)(:13)67.79(8,1!1,八广!〇,7.77~7.72(111,2!1,八广 H),7.54~7.48(m,4H,Ar-H),4.32(q,J = 7.1Hz,2H,CH3CH2-),2.82(s,3H,CH3-),2.58(s, 3H,CH3-),1 · 15(t,J = 7.1Hz,3H,CH3CH2-) ;13C 匪R(126MHz,CDC13)S167.16,151.63, 143.72,142.61,142.15,138.20,137.84,137.57,132.82,129.31,128.57,128.56,128.55, 125.96,62.03,22.04,17.04,13.71.
[0051 ] 实施例10
[0052]
化合物为黄色固体,产率87%,m. p. 154~155°C .其合成方法 同实施例 1,结构数据表征为:4 NMR(500MHz,CDC13)δ 1 · 19(t,J = 7 · 2Hz,3H,CH3CH2-),4 · 09 (s,3H,CH3〇-),4.10(s,3H,CH3〇-),4.33(q,J = 7.2Hz,2H,CH3CH2-),7.46(s,lH,Ar-H) ,7.50 ~7.52(m,4H,Ar-H),7.69~7.71(m,2H,Ar-H);13CNMR(125MHz,CDCl 3)Sl3.78,55.51, 56.55,62.15,106.57,106.76,128.50,128.53,129.08,137.40,138.42,140.04,142.69, 150.55,153.48,154.50,166.92.
[0053] 实施例11
[0054]
化合物为白色固体,产率83%,m.p.105~106°C.其合成方法同实 施例 1,结构数据表征为NMR(500MHz,CDCl3)S9.32(dd,J = 6.6,2.9Hz,lH,Ar-H),8.07 (q,J = 9.1Hz,2H,Ar-H) ,7.96(dd,J = 6.0,3.1Hz,lH,Ar-H) ,7.89(dd,J = 7.6,1.7Hz,2H, Ar-H),7.81~7.76(m,2H,Ar-H),7.59~7.53(m,3H,Ar-H),4.40(q,J = 7.1Hz,2H,CH3CH2-), 1.24(t,J = 7.1Hz,3H,CH3CH2-);13C NMR( 126MHz,αχη3)δ167·06,150.69,144.61,141.19, 139.66,138.11,134.02, 132.33,130.52,129.66,129.48,128.97,128.55,128.07, 127.74,126.36,125.18,62.32,13.79.
[0055] 实施例12
[0056]
化合物为黄色固体,产率82 %,m. p. 59~60°C .其合成方法同 实施例 1,结构数据表征为:4 匪R(500MHz,CDC13)δ 1 · 51 (t,J = 7 · 1Hz,3H,CH3CH2-),2 · 94 (s,3H,CH3-) ,3.97( s,3H,CH3〇-) ,4.57 (q,J = 7.1Hz,2H, CH3CH2-) ,7.47 (dd,J = 5.7Hz, 2.7Hz, lH,Ar-H),7.50(d,J = 2.8Hz,lH,Ar-H),7.93(d, J = 9.4Hz, lH,Ar-H) ;13C 匪R (125MHz,CDC13)514.30,22.43,55.90,62.41,106.74,125.50,129.31,138.92,141.49, 144.00,150.27,160.61,165.83.HRMS(APCI) :m/z[M+H]+calcd for C13H15N2O3:247.1083 ; found :247.1079.
[0057] 实施例13
[0058]
化合物为白色固体,产率85 %,m. p. 50-51 °C .其合成方法 同实施例1,结构数据表征为匪R(600MHz,CDCl3)S7.92(d,J = 9.1Hz,Ar-H,lH),7.44 (dd ,J = 9.1,2.8Hz,Ar-H,lH),7.42(d ,J = 2.7Hz,Ar-H,lH),4.53(q J = 7.1Hz,CH3CH2,2H), 3.93(s,CH30,3H) ,3.20(q J = 7.5Hz,CH3CH2,2H),1.47(t J = 7.1Hz,CH3CH2,3H),1.38(t,J =7 · 5Hz,CH3CH2,3H) · 13C 匪R( 151MHz,CDC13)S166 · 17,160 · 70,154· 62,144· 47,141 · 48, 139.13,129.64,125.30,106.77,62.51,55.98,29.19,14.38,13.59.HRMS(APCI):m/z[M+H ] +calcd for C14H17N2O3:261.1239;found:261.1226.
[0059] 实施例14
[0060]
化合物为白色固体,产率84% ,m.p.ll3-115°C.其合成方法同 实施例 1,结构数据表征为:? NMR(600MHz,CDCl3)S7.89(d,J = 9.1Hz,Ar-H,lH),7.43-7.37 (m,Ar-H,2H),4 · 50(q,J = 7 · 1Hz,CH3CH2,2H),3 · 90(s,CH3O,3H),3 · 14-3 · 10(m,CH3CH2CH2, 2H),1 · 84-1 · 75 (m,CH3CH2CH2,2H),1 · 43 (d,J = 7 · 1H
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