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含4-氧代喹唑啉-2-基的查耳酮類似物及其制備方法和用圖_5

文檔序號:9742275閱讀:來源:國知局
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[0209] 實施例23
[0210] (E)-2-(3-(3-甲氧基苯基)丙烯?;?喹唑啉-4(3H)_酮(化合物23)
[0211] 收率:47%,棕色固體,m.p. 169-1711.? 匪R(600MHz,DMS0-d6M:3.85(s,3H, OCH3),7.10(dd,J=7.8,1.2Hz,lH,Ph 4'-H),7.44(m,3H,Ph2'-H,5'-H,6'-H),7.69(td,J = 7.8,1.2Hz,lH,Quin 6-H),7.91(d,J= 16.2Hz,1H,=CHC0),7.94(m,2H,Quin 7-H,8-H), 8.10(d,J=16.2Hz,lH,=CH),8.22(d,J = 7.8Hz,lH,Quin5-H),12.42(s,lH,NH).ESI-HRMS m/z: CisHi5N2〇3( [M+H] + )計算值:307 · 1083;實測值:307 · 1080 ·
[0212] 實施例24
[0213] (E)-2-(3-(4-甲氧基苯基)丙烯?;?喹唑啉-4(3H)_酮(化合物24)
[0214] 收率:43%,黃色固體,m.p. 189-1921.? 匪R(600MHz,DMS0-d6M:3.85(s,3H, 0CH3),7.07(d,J = 8.4Hz,2H,Ph 3'-H,5'-H),7.68(m,lH,Quin6-H),7.84(d,J = 8.4Hz,2H, Ph 2'-H,6'-H),7.91(d,J = 16.2Hz,lH,=CHC0),7.93(m,2H,Quin 7-H,Quin 8-Η),7·98 (d ,J= 16.2Hz, 1H,=CH), 8.22(d,J = 7.8Hz,lH, Quin 5-H), 12.35(s, ΙΗ,ΝΗ) .ESI-HRMS m/ z: Ci8Hi5N2〇3( [M+H] + )計算值:307 · 1083;實測值:307 · 1080 ·
[0215] 實施例25
[0216] (E)-2-(3-(2,4-二甲氧基苯基)丙烯酰基)喹挫啉-4(3H)_酮(化合物25)
[0217]收率:46%,黃色固體,111.口.180-182°(3.111匪1?(6001抱,0150-(16)3 :3.87(8,3!1,4'-0CH3) ,3.95(s,3H,2,-0CH3),6.67(dd ,J = 8.4,2.4Hz,lH,5,-H) ,6.69(d ,J = 2.4Hz , lH,Ph 3'-H),7.67(m,lH,Quin6-H),7.81(d,J=8.4Hz,lH,Ph6'-H),7.93(m,2H,Quin7-H,8-H),8.04(d ,J= 16.2Hz, 1H,=CHC0), 8.12(d,J= 16.2Hz, 1H,=CH), 8.21 (d,J = 7.8Hz,lH, Quin 5-H), 12 · 28(s, 1H,NH) · ESI-HRMS m/z : Ci9Hi7N2〇4( [M+H] + )計算值:337 · 1188;實測值: 337.1187.
[0218] 實施例26
[0219] (E)-2-(3-(3,4-二甲氧基苯基)丙烯酰基)喹唑啉-4(3H)_酮(化合物26)
[0220] 收率51%,黃色固體,1114.184-186。(3.111匪1?(6001抱,0150-(16)3:3.85(8,3!1,4'-0CH3),3.88(s,3H,3'-0CH 3),7.09(d,J = 8.4Hz,lH,Ph5'-H),(dd,J = 8.4,1.8Hz,lH,6'-H) ,7.46( J=1.8Hz,lH,Ph 2'-Η),7.68(m,lH,Quin 6-H),7.90((1, J= 16.2Hz,1H,=CHC0), 7.94(m,2H,Quin 7-H, 8-H), 7.97(d ,J= 16.2Hz , 1H, =CH), 8.21 (d ,J = 7.8Hz , lH,Quin 5-H) , 12.36( s, ΙΗ,ΝΗ) .ESI-HRMS m/z: Ci9Hi7N2〇4([M+H] + )計算值:337.1188;實測值: 337.1186.
[0221] 實施例27
[0222] (E)-2-(3-(3,5-二甲氧基苯基)丙烯?;?喹唑啉-4(3H)_酮(化合物27)
[0223] 收率:51%,棕色固體,m.p. 181-1851.? 匪R(600MHz,DMS0-d6M:3.83(s,6H, 20CH3),6.66(t,J=1.8Hz,lH,Ph 4'-H),7.02(d,J=1.8Hz,2H,Ph 2'-H,6'-H),7.68(td,J = 7.8,1.2Hz,lH,Quin 6-H), 7.86(d ,J= 15.6Hz , 1H, =CHC0), 7.93( t ,J = 7.8Hz , lH,Quin 7-H) ,7.96(d ,J = 7.8Hz,lH,Quin8-H) ,8.07(d ,J= 15.6Hz , 1H, =CH), 8.22(d ,J = 7.8Hz , 1H,Quin 5-H), 12 · 42(s, ΙΗ,ΝΗ) .ESI-HRMS m/z: Ci9Hi7N2〇4( [M+H] + )計算值:337 · 1188;實測 值:337.1186.
[0224] 實施例28
[0225] (E)-2-(3-(3,4-亞乙基二氧苯基)丙烯酰基)喹唑啉-4(3H)_酮(化合物28)
[0226] 收率:32%,黃色固體,m.p. 193-1951.? 匪R(600MHz,DMS0-d6M:4.32(m,4H, OCH2CH2O),6.98(d,J = 8.4Hz,lH,Ph 5'-H),7.39(d,J = 8.4Hz,lH,6'-H),7.40(s,lH,Ph 2'-H),7.68(td,J = 7.8,1.8Hz,lH,Quin 6-H),7.84(d,J=16.2Hz,lH,=CH⑶),7.94(m, 2H,Quin 7-H,Quin 8-H) ,7.95(d ,J = 16.2Hz, 1H, =CH) ,8.21 (d ,J = 7.8Hz , lH,Quin 5-H), 12 · 35(s, 1H,NH) ·ESI-HRMS m/z: Ci9Hi5N2〇4( [M+H] + )計算值:335 · 1032;實測值:335 · 1025 ·
[0227] 實施例29
[0228] (E)-2-(3-(3,4,5-三甲氧基苯基)丙烯?;?喹唑啉-4(3H)_酮(化合物29)
[0229] 收率:33%,黃色固體,1114.189-193°(3.111匪1?(6001抱,0150-(16)3:3.74(8,3!1,4'-0CH 3),3.89(s,6H,3'-0CH3,5'-0CH3),7.21(s,2H,Ph 2'-H,6'-H),7.68(t,J = 7.8Hz,lH, Quin 6-H),7.89(d,J=15.6Hz,lH,=CH⑶),7.94(m,2H,Quin 7-H,8-H),8.01(d,J = 15.6Hz,lH,=CH) ,8.22 (d,J = 7.8,1H, Quin 5-H) , 12.39(s , ΙΗ,ΝΗ) .ESI-HRMS m/z: C20H19N2〇5 ([M+H] +)計算值:367 · 1294;實測值:367 · 1291 ·
[0230] 實施例30
[0231] (E)-2-(3_(4-甲基苯基)丙烯?;?喹唑啉-4(3H)_酮(化合物30)
[0232] 收率:39% ,橙色固體,m.p. 186-1891.? 匪R(600MHz,DMS0-d6M:2.38(s,3H, CH3),7.33(d,J = 7.8Hz,2H,Ph 3'-H,5'-H),7.68(m,lH,Quin6-H),7.96(d,J = 7.8Hz,2H, Ph 2,-H,6,-H) ,7.91 (d,J= 16.2Hz, 1H,=CHC0),7.94(m,2H,Quin 7-H,8-H) ,8.07(d,J = 16.2Hz,lH,=CH) ,8.22 (d,J = 7.8,1H, Quin 5-H) , 12.39(s , ΙΗ,ΝΗ) .ESI-HRMS m/z : C18H15N2〇2( [M+H] + )計算值:291 · 1134;實測值:291 · 1132 ·
[0233] 實施例31
[0234] (E)-2-(3_(4-溴苯基)丙烯酰基)喹唑啉-4(3H)_酮(化合物31)
[0235] 收率:68% ,淺黃色固體,m·p · 202-205°C · 4 NMR(600MHz ,DMS〇-d6)δ : 7 · 69(m, 1H, Quin 6-H),7.71(d,J = 8.4Hz,2H,Ph 3'-H,5'-H),7.83(d,J = 8.4Hz,2H,Ph 2'-H,6'-H), 7.91(d,J=16.2Hz,lH,=CHC0),7.94(m,2H,Quin 7-H,8-H),8.12(d,J=16.2Hz,lH,= CH),8.22(d,J = 7.8, lH,Quin 5-H),12.43(s,lH,NH) .ESI-HRMS m/z:Ci7Hi2BrN2〇2([M+H] + ) 計算值:355 · 0082,357 · 0062;實測值:355 · 0076,357 · 0060 ·
[0236] 實施例32
[0237] (E)-2-(3_(4-氯苯基)丙烯?;?喹唑啉-4(3H)_酮(化合物32)
[0238] 收率:46 %,淺黃色固體,m · p · 198-201°C · 4 MMR(600MHz,DMS〇-d6) δ: 7 · 57(d,J = 8.4Hz,2H,Ph 3'-H,5'-H),7.69(m,lH,Quin 6-H),7.91(d,J=8.4Hz,2H,Ph 2'-H,6'-H), 7.92(m,3H,Quin 7-H,8-H,=CH⑶),8. ll(d,J=16.2Hz,lH,=CH),8.22(d,J = 7.8,lH, Quin 5-H) ,12.43( s,lH,NH) .ESI-HRMS m/z: Ci7Hi2ClN2〇2([M+H] + )計算值:311.0587, 313 · 0558;實測值:311 · 0587,313 · 0569.
[0239] 實施例33
[0240] (E)-2-(3-(2,4-二氯苯基)丙烯?;?喹唑啉-4(3H)_酮(化合物33)
[0241 ]收率:69 %,粉色固體,m · p · 200-202°C · 4 MMR( 600MHz,DMS〇-d6) δ : 7 · 58 (dd,J = 8.4,1.8Hz,lH,Ph 5'-H),7.69(td,J = 7.8,1.2Hz,lH,Quin6-H),7.82(d,J=1.8Hz,lH,Ph 3'-H),7.92(d,J = 7.8Hz,lH,Quin 8-H),7.94(td,J = 7.8,1.2Hz,lH,Quin 7-H),8.12(d,J = 16.2Hz,lH,=CH⑶),8.13(d,J = 8.4Hz,lH,Ph 6'-H),8.17((1, J= 16.2Hz,1H,=CH), 8 · 22(d,J = 7 · 8,1H,Quin 5-H),12 · 49(s,1H,NH) · ESI-HRMS m/z : C17H11CI2N2O2([M+H] + )計算 值:345 · 1884,347 · 0168;實測值:345 · 0193,347 · 0165.
[0242] 實施例34
[0243] (E)-2-(3-(4-氟苯基)丙烯?;?喹唑啉-4(3H)_酮(化合物34)
[0244] 收率:31%,粉色固體,1114.189-1931.? 匪R(600MHz,DMS0-d6M:7.35(d,J = 8.4Hz,2H,Ph 3'-H,5'-H),7.68(m,lH,Quin 6-H),7.94(d,J = 16.2Hz,lH,=CHC0) ,7.95 (m,4H,Ph 2,-H,6'-H,Quin 7-H,8-H),8.06(d,J= 16.2Hz,1H,=CH),8.22((1, J = 7.8Hz, lH,Quin 5-H),12.41(s, ΙΗ,ΝΗ) .ESI-HRMS m/z:Ci7Hi2FN2〇2([M+H] + )計算值:295.0883;實 測值:295.0882.
[0245] 實施例35
[0246] (E)-2-(3-(4-氰基苯基)丙烯酰基)喹唑啉-4(3H)_酮(化合物35)
[0247] 收率:61% ,粉色固體,1114.200-2021.? 匪R(600MHz,DMS0-d6)S: 7.69(m,lH, Quin 6-H),7.95(m,3H,=OTCO,Quin7-H,8-H),7.96(d,J = 7.8Hz,2H,Ph2,-H,6,-H), 8.06(d,J = 7.8Hz,2H,Ph 3'-H,5'-H),8.21(d,J=16.2Hz,lH,=CH),8.22(d,J = 7.8Hz, 1H,Quin 5-H),12 · 48(s,ΙΗ,ΝΗ) .ESI-HRMS m/z: Ci8Hi2N3〇2( [M+H] + )計算值:302 · 0930;實測 值:302.0926.
[0248] 實施例36
[0249] (E)-2-(3-(4-硝基苯基)丙烯酰基)喹唑啉-4(3H)_酮(化合物36)
[0250] 收率:69 %,淺黃色固體,m · p · 206-209°C · 4 NMR(600MHz,DMS〇-d6) δ : 7 · 70 (m,1H, Quin 6-H) ,7.95(m,2H,Quin 7-H,8-H),8.01(d,J= 16.2Hz,lH,=CH⑶),8· 15(d,J = 8.4Hz,2H,Ph 2'-H,6'-H),8.23(d,J = 8.4,lH,Quin 5-H),8.25(d,J=16.2Hz,lH,=CH), 8.32(d,J = 8.4Hz,2H,Ph3'-H,5'-H),12.50(s,lH,NH).ESI-HRMS m/z:Ci7Hi2N3〇4([M+H] + ) 計算值:322 · 0828;實測值:322 · 0826 ·
[0251] 實施例37
[0252] (E)-2-(3-(呋喃-2-基)丙烯?;?喹唑啉-4(3H)_酮(化合物37)
[0253] 收率:65%,黃色固體,1114.187-1901.? NMR(600MHz,DMS0-d6)S:6.75(dd,J = 6.0,1.8Hz,lH,furan-2-yl 4'-H),7.20(d,J = 5.4Hz,lH,furan-2-yl 3'-H),7.68(td,J = 7.8,1.8Hz,lH,Quin 6-H),7.73(d,J=15.6Hz,lH,=CHC0),7.87(d,J=15.6Hz,lH,=CH), 7.93(m,2H,Quin 7-H,8-H),8.01(d,J=1.2Hz,lH,furan-2-yl 5'-H),8.21(d,J = 7.8,lH, Quin 5-H),12 · 36 (s,1H,NH) · ESI-HRMS m/z : C15H11N2O3 ([M+H] + )計算值:267 · 0
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