一种噻吩联吡咯啉酮类化合物、制备方法及应用_4

文档序号:9465654阅读:来源:国知局
,CHS),7. 32 (d, J = 4.8Hz,lH,CH = C),7.25(d,J = 8.4Hz,4H,ArH),7.12(t,J = 8.6Hz,2H,ArH), 6. 99-6. 85 (m,1H,CH = CHS),5. 40 (s,2H,CH2O),4. 37 (s,2H,CH2N) ·
[0095] 3-(噻吩-2-基)-4-(2-(4-氯苯基)-2-(2-(4-溴苯基)亚肼基)乙氧基)-l, 5-二氢-2H-吡咯-2-酮(C7):
[0096] 淡黄色粉末,收率 91. 4%,mp 144. 6-145. 4Γ NMR(400MHz,DMS0) δ :10. 25(s, 1H,ArNH),7· 99(s,1H,CONH),7· 89(d,J = 8. 6Hz,2H,ArH),7· 46(dd,J = 10. 3,8· 9Hz,4H, ArH),7. 40 (d,J = 3. 3Hz,1H,CHS),7. 32 (d,J = 4. 9Hz,1H,CH = C),7. 22 (d,J = 8. 8Hz, 2H,ArH),6. 93(dd,J = 8. 8,4. 8Hz,1H,CH = CHS),5. 40(s,2H,CH2O),4. 37(s,2H,CH2N).
[0097] 3-(噻吩-2-基)-4-(2-(4-溴苯基)-2-(2-(4-溴苯基)亚肼基)乙氧基)_1, 5-二氢-2H-吡咯-2-酮(C 8):
[0098] 白色粉末,收率 92. 5%,mp 156. 4-159. 2Γ JH NMR(400MHz,DMS0) δ :1〇· 16(s, 1H,ArNH),7· 97 (s,1H,CONH),7· 94-7. 86 (m,2H,ArH),7· 42 (dd,J = 12. 4, 5. 9Hz,3H,ArH, CHS),7· 32(d,J = 4. 9Hz,1H,CH = C),7· 23(dd,J = 20. 2,8· 7Hz,4H,ArH),6· 97-6. 88(m, 1H,CH = CHS),5. 40 (s,2H,CH2O),4. 37 (s,2H,CH2N) ·
[0099] 3-(噻吩-2-基)-4-(2-(2,4-二氯苯基)-2-(2-(4-溴苯基)亚肼基)乙氧基)_1, 5-二氢-2H-吡咯-2-酮(C 9):
[0100] 淡黄色粉末,收率 44. 4%,mp 152. 4-154. 6°C NMR(400MHz,DMS0) δ :10. 〇l(s, 1H,ArNH),7· 95 (s,1H,CONH),7· 68 (d,J = I. 5Hz,1H,ArH),7· 61 (d,J = 8. 3Hz,1H,ArH), 7.51(dd,J = 8.3,1.5Hz,lH,CHS),7.41(d,J = 8.7Hz,2H,ArH),7.30(d,J = 5. 1Hz,1H,CH =C),7. 11 (d,J = 8. 7Hz,2H,ArH),7. 02 (d,J = 3. 5Hz,1H,ArH),6. 90-6. 78 (m,1H,CH = CHS),5. 37 (s,2H,CH2O),4. 26 (s,2H,CH2N) ·
[0101] I-甲基-3-(噻吩-2-基)-4- (2- (4-甲基苯基)-2- (2- (2-氯苯基)亚肼基)乙 氧基)-1,5-二氢-2H-吡咯-2-酮(D1):
[0102] 浅褐色粉末,收率 31. 0%,mp 140. 7-143. 9°C JH NMR(400MHz,DMS0) δ :9· 14(s, 1Η,ArNH),7. 82 (d,J = 8. 0Hz,2Η,ArH),7. 65 (d,J = 8. 0Hz,1Η,ArH),7. 48 (d,J = 2. 8Hz, 1H,CHS),7· 39-7. 30 (m,3H,CH = C,ArH),7· 27 (d,J = 7. 9Hz,2H,ArH),7· 00-6. 94 (m,1H, CH = CHS),6. 90 (t,J = 7. 5Hz,1H,ArH),5. 57 (s,2H,CH2O),4. 47 (s,2H,CH2N),2. 97 (s,3H, NCH3),2. 35(s,2H,ArCH3).
[0103] I-甲基-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)-1,5-二氢-2H-吡咯-2-酮(D 2):
[0104] 浅灰色粉末,收率 40. 5%,mp 173. 4-176. 8°C JH NMR(400MHz,DMS0) δ :9· 99 (s, 1Η,ArNH),7· 74(d,J = 8. 2Hz,2H,ArH),7· 43-7. 38(m,1Η,CHS),7· 31(dd,J = 5· 1,0· 9Hz, 1Η,CH = C),7· 21 (d,J = 8· IHz,2Η,ArH),7· 16 (d,J = 8· 4Ηζ,2Η,ArH),7· 07 (d,J = 8· 4Ηζ, 2Η,ArH),6· 93(dd,J = 5· 1,3· 7Hz,1Η,CH = CHS),5· 40(s,2H,CH2O),4· 49(s,2H,CH2N), 2· 99 (s,3Η,NCH3),2· 32 (s,3Η,ArCH3),2· 23 (s,3Η,NHArCH3) ·
[0105] 1-甲基-3-(噻吩-2-基)-4- (2- (4-甲基苯基)-2- (2- (4-氯苯基)亚肼基)乙 氧基)-1,5-二氢-2Η-吡咯-2-酮(D3):
[0106] 白色粉末,收率 57.8%,mp 156.5_158.9°C JH NMR(400MHz,DMS0) δ :l〇.〇8(s, 1H,ArNH),7· 76 (d,J = 7. 7Hz,2H,ArH),7· 41 (d,J = I. 8Hz,1H,CHS),7· 31 (d,J = 8. 5Hz, 3H,CH = C,ArH),7. 28-7. 16 (m,4H,ArH),7. 00-6. 87 (m,1H,CH = CHS),5. 37 (s,2H,CH2O), 4. 45 (s,2H,CH2N),2. 99 (s,3H,NCH3),2. 32 (s,3H,ArCH3) ·
[0107] I-甲基-3-(噻吩-2-基)-4- (2- (4-甲基苯基)-2- (2- (4-溴苯基)亚肼基)乙 氧基)- I,5-二氢-2H-吡咯-2-酮(D4):
[0108] 白色粉末,收率 62. 2%,mp 168. 8-169. 7°C JH NMR(400MHz,DMS0) δ :10. 12(s, 1H,ArNH),7· 77(d,J = 7. 2Hz,2H,ArH),7· 44(d,J = 8. 3Hz,3H,CHS,ArH),7· 33(d,J = 3. 2Hz,1H,CH = C),7. 22 (s,4H,ArH),6. 94 (s,1H,CH = CHS),5. 38 (s,2H,CH2O),4. 47 (s,2H, CH2N),3. 00 (s,3H,NCH3),2. 33 (s,3H,)·
[0109] I-甲基-3-(噻吩-2-基)-4-(2-(4-氟苯基)-2-(2-(4-氟苯基)亚肼基)乙氧 基)-1,5-二氢-2H-吡咯-2-酮(E 1):
[0110] 浅灰色粉末,收率 80. 2%,mp 147. 4-149. 3°C NMR(400MHz,DMS0) δ :10. 12(S, 1H,ArNH),7· 89 (dd,J = 8· 3, 5. 7Hz,2H,ArH),7· 41 (d,J = 2. 8Hz,1H,CHS),7· 32 (d,J = 4. 9Hz,1H,CH = C),7. 25(dt,J = 13. 7,6. 8Hz,4H,ArH),7. 12(t,J = 8. 8Hz,2H,ArH), 6. 96-6. 89 (m,1H,CH = CHS),5. 41 (s,2H,CH2O),4. 47 (s,2H,CH2N),2. 99 (s,3H,NCH3) ·
[0111] I-甲基-3-(噻吩-2-基)-4-(2-(4-氟苯基)-2-(2-(4-溴苯基)亚肼基)乙氧 基)-1,5-二氢-2H-吡咯-2-酮(E 2):
[0112] 白色粉末,收率 71.5%,mp 166.0_167.2°C JH NMR(400MHz,DMS0) δ :10. 17(s, 1H, ArNH) ,7. 90 (dd, J = 8. 7,5. 6Hz,2H, ArH), 7. 44 (d, J = 8. 8Hz,2H, ArH), 7. 40 (d, J = 3. 6Hz,1H,CHS),7· 32(d,J = 5. 1Hz,1H,CH = C),7· 29-7. 16(m,4H,ArH),6· 94(dd,J = 5. 0, 3. 8Hz,1H,CH = CHS),5. 39 (s,2H,CH2O),4. 45 (s,2H,CH2N),2. 99 (s,3H,NCH3) ·
[0113] I-甲基-3-(噻吩-2-基)-4- (2- (4-氟苯基)-2- (2- (4-三氟甲基苯基)亚肼基) 乙氧基)-1,5-二氢-2H-吡咯-2-酮(E3):
[0114] 白色粉末,收率 83. 3%,mp 162. 2-163. 5cC JH NMR(400MHz,DMS0) δ :1〇· 43 (s, lH,ArNH),7.94(dd,J = 8.7,5.6Hz,2H,ArH),7.62(d,J = 8.6Hz,2H,ArH),7.40(d, δ = 8. 8Hz,3H,CHS),7· 32 (d,J = 5. 1Hz,1H,CH = C),7· 28 (t,J = 8. 8Hz,2H,ArH), 7. 00-6. 84 (m,1H,CH = CHS),5. 43 (s,2H,CH2O),4. 46 (s,2H,CH2N),3. 00 (s,3H,NCH3) ·
[0115] I-甲基-3-(噻吩-2-基)-4- (2- (4-氯苯基)-2- (2- (4-溴苯基)亚肼基)乙氧 基)-1,5-二氢-2H-吡咯-2-酮(E4):
[0116] 浅褐色粉末,收率 51. 2%,mp 169. 3-169. 9°C NMR(400MHz,DMS0) δ :10. 26(s, 1H,ArNH),7.88(d,J = 8·6Ηζ,2Η,ArH),7.51-7.42(m,4H,ArH),7.41(d,J = 3·4Ηζ,1Η, CHS),7· 32(d,J = 4. 9Hz,1H,CH = C),7· 22(d,J = 8. 8Hz,2H,ArH),6· 97-6. 91(m,1H,CH = CHS),5. 39 (s,2H,CH2O),4. 46 (s,2H,CH2N),2. 99 (s,3H,NCH3) ·
[0117] 5-甲基-3-(噻吩-2-基)-4- (2- (4-氟苯基)-2- (2- (4-溴苯基)亚肼基)乙氧 基)-1,5-二氢-2H-吡咯-2-酮(F1):
[0118] 紫色粉末,收率 29. 8%,mp 135. 1-139. 8°C ^HNMRGOOMHz,DMsO) δ :10. 23(s, 1H,ArNH),8· 05(s,1H,C0NH),7· 91-7. 82(m,2H,ArH),7· 37(d,J = 5. 2Hz,2H,CHS,ArH), 7. 20 (dd,J = 8. 8, 3. 3 Hz. 4H,CH = C,ArH),7. 06-7. 01 (m,3H,ArH,CH = CHS),4. 17 (dd,J =13. 6,6. 9Hz, 1H, CH3CH), 3. 96(s,2H, CH2O), I. 37 (d, J = 6. 9Hz,3H, CH3CH).
[0119] 5-甲基-3-(噻吩-2-基)-4- (2- (4-氟苯基)-2- (2- (4-三氟甲基苯基)亚肼基) 乙氧基)-1,5-二氢-2H-吡咯-2-酮(F2):
[0120] 浅粉色粉末,收率 54. 7%,mp 142. 9-146. 7°C NMR(400MHz,DMS0) δ :10. 44(s, 1H,ArNH),8. 10(s,lH
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