一种噻吩联吡咯啉酮类化合物、制备方法及应用_2

文档序号:9465654阅读:来源:国知局
· 97 (s,1Η,CONH),7· 77 (d,J = 8. 1Hz,2Η,ArH),7· 42 (d,J = 3. 1Hz,1Η,CHS), 7. 36-7. 14(m,7H,CH = CS,ArH),6. 93(dd,J = 4. 9,3. 8Hz,1H,ArH),6. 83(t,J = 6. 5Hz, 1H,CH = CHS),5. 40 (s,2H,CH2O),4. 38 (s,2H,CH2N),2. 32 (s,3H,ArCH3) ·
[0045] 3-(噻吩-2-基)-4- (2- (4-甲基苯基)-2- (2- (2-氟苯基)亚肼基)乙氧基)-I, 5-二氢-2H-吡咯-2-酮(A2):
[0046] 白色粉末,收率 51. l%,mp 158. 1-159. 6°C NMR(400MHz,DMS0) δ :9. 54(s,1H, ArNH),7· 95 (s,1H,CONH),7· 79 (d,J = 8. 2Hz,2H,ArH),7· 62 (td,J = 8· 5,1. 4Hz,1H,ArH), 7. 44-7. 39 (m,1H,CHS),7. 32 (dd,J = 5. I,0· 9Hz,1H,CH = C),7. 24 (d,J = 8. IHz,2H,ArH), 7.21-7. ll(m,2H,ArH),6.93(dd,J = 5. 1,3·7Ηζ,1Η,ArH),6.91-6.82(m,lH,CH = CHS), 5. 51 (s,2H,CH2O),4. 35 (s,2H,CH2N),2. 33 (s,3H,ArCH3) ·
[0047] 3-(噻吩-2-基)-4- (2- (4-甲基苯基)-2- (2- (2-氯苯基)亚肼基)乙氧基)-I, 5-二氢-2H-吡咯-2-酮(A3):
[0048] 白色粉末,收率 30. 2%,mp 160. 2-162. 6°C JH NMR(400MHz,DMS0) δ :9· 12 (s, 1Η,ArNH),7· 99(s,1Η,CONH),7· 82(d,J = 8. 2Hz,2H,ArH),7· 64(d,J = 7. 2Hz,1Η,ArH), 7· 48 (d,J = 2· 9Hz,1Η,CHS),7· 39-7. 29 (m,3Η,CH = C,ArH),7· 26 (d,J = 8· ΙΗζ,2Η,ArH), 6· 96(dd,J = 5· 0,3· 7Hz,lH,ArH),6· 92-6. 85(m,1H,CH = CHS),5· 58(s,2H,CH20),4· 35(s, 2Η,CH2N),2. 34 (s,3Η,ArCH3).
[0049] 3-(噻吩-2-基)-4- (2- (4-甲基苯基)-2- (2- (3-氯苯基)亚肼基)乙氧基)-I, 5-二氢-2H-吡咯-2-酮(A4):
[0050] 白色粉末,收率 37.5%,mp 172.2-174.4°C JH NMR(400MHz,DMS0) δ :10. 12(s, 1H,ArNH),7· 97 (s,1H,CONH),7· 77 (d,J = 8. 2Hz,2H,ArH),7· 41 (d,J = 2. 8Hz,1H,CHS), 7. 32(d,J = 5. 1Hz,1H,CH = C),7. 31-7. 21(m,4H,ArH),7. 18(d,J = 8. 2Hz,lH,ArH), 6. 93(dd,J = 5. 0,3. 7Hz,1H,ArH),6. 85(dd,J = 7. 8,1. 1Hz,1H,CH = CHS),5. 39(s,2H, CH2O),4. 37 (s,2H,CH2N),2. 33 (s,3H,ArCH3) ·
[0051] 3-(噻吩-2-基)-4- (2- (4-甲基苯基)-2- (2- (4-甲基苯基)亚肼基)乙氧基)-I, 5-二氢-2H-吡咯-2-酮(A5):
[0052] 白色粉末,收率 42. 3%,mp 140. 7-142. 2°C JH NMR(400MHz,DMS0) δ :9· 90 (s, 1Η,ArNH),7· 98 (s,1Η,CONH),7· 75 (d,J = 7. 9Hz,2Η,ArH),7· 42 (d,J = 3. 0Hz,1Η,CHS), 7· 31(d,J = 5· 0Hz,1H,CH = C),7· 21(d,J = 7· 9Hz,2H,ArH),7· 15(d,J = 8· lHz,2H,ArH), 7· 08(d,J = 8· lHz,2H,ArH),6· 93(t,J = 4· 2Hz,1H,CH = CHS),5· 38(s,2H,CH20),4· 38(s, 2Η,CH2N),2· 32 (s,3Η,NHArCH3),2· 23 (s,3Η,CArCH3) ·
[0053] 3-(噻吩-2-基)-4-(2-(4-甲基苯基)-2-(2-(4-甲氧基苯基)亚肼基)乙氧 基)-1,5-二氢-2H-吡咯-2-酮(A 6):
[0054] 淡黄色粉末,收率 37. 7%,mp 139. 5-142. 8°C NMR(400MHz,DMS0) δ :1〇· 〇5(s, 1H,ArNH),7· 99 (s,1H,CONH),7· 76 (d,J = 8. 0Hz,2H,ArH),7· 41 (d,J = 3· 3 Hz,1H,CHS), 7. 32(d,J = 5. 0Hz,1H,CH = C),7. 28-7. 18(m,4H,ArH),7. 13(dd,J = 19. 0,10. 2Hz,2H, ArH),6. 95-6. 90 (m,1H,CH = CHS),5. 40 (s,2H,CH2O),4. 39 (s,2H,CH2N),2. 32 (s,3H,ArCH3) ·
[0055] 3-(噻吩-2-基)-4- (2- (4-甲基苯基)-2- (2- (4-氟苯基)亚肼基)乙氧基)-I, 5-二氢-2H-吡咯-2-酮(A7):
[0056] 白色粉末,收率 62. 5%,mp 149. 3-151. 2Γ JH NMR(400MHz,DMS0) δ :1〇· l〇(s, 1H,ArNH),7· 98 (s,1H,CONH),7· 78 (d,J = 7. 9Hz,2H,ArH),7· 42 (d,J = 2. 7Hz,1H,CHS), 7. 32 (d,J = 8. 8Hz,3H,CH = C,ArH),7. 29-7. 13 (m,4H,ArH),7. 00-6. 86 (m,1H,CH = CHS), 5. 40 (s,2H,CH2O),4. 38 (s,2H,CH2N),2. 33 (s,3H,ArCH3) ·
[0057] 3-(噻吩-2-基)-4- (2- (4-甲基苯基)-2- (2- (4-氯苯基)亚肼基)乙氧基)-I, 5-二氢-2H-吡咯-2-酮(A8):
[0058] 白色粉末,收率 61. 2%,mp 155. 8-156. %~ JH NMR(400MHz,DMS0) δ :1〇· l〇(s, 1H,ArNH),7· 98 (s,1H,CONH),7· 78 (d,J = 7. 9Hz,2H,ArH),7· 42 (d,J = 2. 7Hz,1H,CHS), 7. 32 (d,J = 8. 8Hz,3H,CH = C,ArH),7. 29-7. 13 (m,4H,ArH),7. 00-6. 86 (m,1H,CH = CHS), 5. 40 (s,2H,CH2O),4. 38 (s,2H,CH2N),2. 33 (s,3H,ArCH3) ·
[0059] 3-(噻吩-2-基)-4-(2-(4-甲基苯基)2-(2-(4-溴苯基)亚肼基)乙氧基)-1, 5-二氢-2H-吡咯-2-酮(A9):
[0060] 白色粉末,收率 72.3%,mp 159.9-162. 1°C JH NMR(400MHz,DMS0) δ :l〇.〇9(s, 1H,ArNH),7· 97(s,1H,CONH),7· 77 (d,J = 8. 1Hz,2H,ArH),7· 42 (d,J = 8. 7Hz,3H,CHS, ArH),7. 31(d,J = 5. 0Hz,1H,CH = C),7. 21(t,J = 8. lHz,4H,ArH),6. 97-6. 83(m,1H,CH = CHS),5. 38 (s,2H,CH2O),4. 37 (s,2H,CH2N),2. 32 (s,3H,ArCH3) ·
[0061] 3-(噻吩-2-基)-4- (2- (4-甲基苯基)-2- (2- (4-三氟甲基苯基)亚肼基)乙氧 基)-1,5-二氢-2H-吡咯-2-酮(A10):
[0062] 白色粉末,收率 82. 3%,mp 167. 0-169. 1°C JH NMR(400MHz,DMS0) δ :1〇· 35 (s, 1Η,ArNH),7. 98 (s,1Η,C0NH),7. 80 (d,J = 7. 7Hz,2Η,ArH),7. 61 (d,J = 8. 3Hz,2Η,ArH), 7.39(d,J = 9.0Hz,3H,CHS,ArH),7.31(d,J = 4.9Hz,lH,CH = C),7.24(d,J = 7·7Ηζ,2Η, ArH),6· 92(d,J = 3. 7Hz,1H,CH = CHS),5· 42(s,2H,CH2O),4· 38(s,2H,CH2N),2· 34(s,3H, ArCH3).
[0063] 3-(噻吩-2-基)-4-(2-(4-甲基苯基)-2-(2-(2,4-二氯苯基)亚肼基)乙氧 基)-1,5-二氢-2H-吡咯-2-酮(A 11):
[0064] 白色粉末,收率 38. 9%,mp 171. 7-173. 6°C JH NMR(400MHz,DMS0) δ :9· 20 (s, 1Η,ArNH),8· 00(s,1Η,CONH),7· 82(d,J = 7. 9Hz,2H,ArH),7· 64(d,J = 8. 9Hz,1Η,ArH), 7· 53(s,lH,ArH),7· 46(d,J = 3· 0Hz,1H,CHS),7· 37(dd,J = 14. 3,6· 9Hz,2H,CH = C,ArH), 7· 26 (d,J = 7· 9Ηζ,2Η,ArH),7· 02-6. 86 (m,1Η,CH = CHS),5· 58 (s,2Η,CH2O),4· 35 (s,2Η, CH2N),2· 34(s,3H,ArCH3).
[0065] 3-(噻吩-2-基)-4-(2-苯基-2-(2-(4-氟苯基)亚肼基)乙氧基)-l,5-二 氢-2H-吡咯-2-酮(B 1):
[0066] 浅灰色粉末,收率 44. 4%,mp 131. 4-132. 2°C NMR(400MHz,DMS0) δ :1〇· 〇5(s, 1H, ArNH), 7. 97 (s, 1H, CONH), 7. 86 (d, J = 7. 8Hz, 2H, ArH), 7. 40 (d, J = 7. 5Hz, 3H, CHS, ArH),7. 32(t,J = 6. 7Hz,2H,CH = C,ArH),7. 28-7. 20(m,2H,ArH),7. 12(t,J = 8. 7Hz,2H, ArH),6. 96-6. 90 (m,1H,CH = CHS),5. 40 (s,2H,CH2O),4. 38 (s,2H,CH2N) ·
[0067] 3-(噻吩-2-基)-4-(2-(2-氯苯基)-2-(2-(4-氟苯基)亚肼基)乙氧基)_1, 5-二氢-2H-吡咯-2-酮(B 2):
[0068] 土黄色粉末,收率 45. 8%,mp 125. 0-126. 8°C JH NMR(400MHz,DMS0) δ :9· 85 (s, lH,ArNH),7.95(s,lH,C0NH),7.58(dd,J = 5.7,3.5Hz,lH,ArH),7.50(dt,J = 7.3, 3. 7Hz,1H,ArH),7· 42 (dd,J = 5· 7, 3. 5Hz,2H,CHS,ArH),7· 28 (d,J = 4. 9Hz,1H,CH = C), 7. 20-7. 06 (m,4H,ArH),7. 04 (d,J = 3. 1Hz,1H,ArH),6. 87-6. 80 (m,1H,C
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