一种噻吩联吡咯啉酮类化合物、制备方法及应用_3

文档序号:9465654阅读:来源:国知局
H = CHS),5. 38 (s, 2H,CH2O),4. 27(s,2H,CH2N).
[0069] 3-(噻吩-2-基)-4-(2-(2-溴苯基)-2-(2-(4-氟苯基)亚肼基)乙氧基)_1, 5-二氢-2H-吡咯-2-酮(B 3):
[0070] 淡绿色粉末,收率 35. 2%,mp 132. 2-135. 6°C JH NMR(400MHz,DMS0) δ :9· 94(s, 1Η,ArNH),7· 96 (s,1Η,CONH),7· 68 (d,J = 7. 9Hz,1Η,ArH),7· 55 (d,J = 6. 2Hz,1Η,CHS), 7.49-7.31(m,4H,ArH),7.28(d,J = 4·9Ηζ,1Η,CH = C),7. ll(d,J = 8·8Ηζ,2Η,ArH), 7. 00 (d,J = 3. 2Hz,1H,ArH),6. 86-6. 79 (m,1H,CH = CHS),5. 37 (s,2H,CH2O),4. 26 (s,2H, CH2N) ·
[0071] 3-(噻吩-2-基)-4-(2-(3-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 4):
[0072] 淡黄色粉末,收率 35.6, mp 125. 2-126. (TC JH NMR (400MHz,DMS0) δ :1〇· 18 (s, 1Η, ArNH), 7. 83 (d, J = 7. 7Hz, 1H, CONH), 7. 43 (t, J = 6. 9Hz, 2H, CHS, ArH), 7. 37 (d, J = 7.7Hz,lH,ArH),7.32(d,J = 5.0Hz,lH,CH = C),7.30-7.21(m,2H,ArH),7.14(t,J = 8. 6Hz,2H,ArH),6. 98-6. 90 (m,1H,CH = CHS),5. 40 (s,2H,CH2O),4. 38 (s,2H,CH2N) ·
[0073] 3-(噻吩-2-基)-4- (2- (4-甲氧基苯基)-2- (2- (4-氟苯基)亚肼基)乙氧基)-I, 5-二氢-2H-吡咯-2-酮(B5):
[0074] 淡黄色粉末,收率 57.9%,mp 153. 4-154. 3°C JH NMR(400MHz,DMS0) δ .9.91 (s, 1Η,ArNH),7· 97 (s,1Η,CONH),7· 80 (d,J = 8. 8Hz,2Η,ArH),7· 42 (d,J = 3. 6Hz,1Η,CHS), 7· 32(d,J = 5· 0Hz,1Η,CH = C),7· 22(dd,J = 9· 0,4· 8Ηζ,2Η,ArH),7· ll(t,J = 8· 8Hz, 2Η,ArH),7· 02-6. 90 (m,3Η,ArH,CH = CHS),5· 38 (s,2Η,CH2O),4· 37 (s,2Η,CH2N),3· 78 (s, 3Η,OCH3).
[0075] 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-2Η-吡咯-2-酮(B 6):
[0076] 浅灰色粉末,收率 67. 2%,mp 133. 7-134. 5°C NMR(400MHz,DMS0) δ :1〇· 〇7(s, 1H, ArNH), 7. 98 (s, 1H, CONH), 7. 94-7. 84 (m, 2H, ArH), 7. 40 (s, 1H, CHS), 7. 32 (d, J = 4. 7Hz, 1H,CH = C),7. 25(d,J = 8. 4Hz,4H,ArH),7. 12(t,J = 8. 5Hz,2H,ArH),6. 97-6. 90(m,1H, CH = CHS),5. 40 (s,2H,CH2O),4. 38 (s,2H,CH2N) ·
[0077] 3-(噻吩-2-基)-4-(2-(4-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 7):
[0078] 淡黄色粉末,收率 82. 5%,mp 131. 2-132. 2°C NMR(400MHz,DMS0) δ :1〇· 19(s, 1H,ArNH),7· 99 (s,1H,CONH),7· 89 (d,J = 8. 6Hz,2H,ArH),7· 46 (d,J = 8. 6Hz,2H,ArH), 7. 41(d,J = 3. 2Hz,1H,CHS),7· 32(d,J = 4. 7Hz,1H,CH = C),7· 27(dd,J = 9· 0,4· 8Hz, 2H,ArH),7. 13(t,J = 8.8Hz,2H,ArH),6.94(dd,J = 4·9,3·8Ηζ,1Η,CH = CHS),5.41(s, 2H,CH2O),4. 39(s,2H,CH2N).
[0079] 3-(噻吩-2-基)-4-(2-(4-溴苯基)-2-(2-(4-氟苯基)亚肼基)乙氧基)_1, 5-二氢-2H-吡咯-2-酮(B 8):
[0080] 浅灰色粉末,收率 87. 5%,mp 136. 1-138. 7°C NMR(400MHz,DMS0) δ :1〇· 16(s, 1H, ArNH), 7. 98 (s, 1H, CONH), 7. 91 (dd, J = 8. 6, 5. 6Hz, 2H, ArH), 7. 43 (d, J = 8. 7Hz, 2H, ArH),7. 40 (d,J = 3. 2Hz,1H,CHS),7. 32 (d,J = 4. 9Hz,1H,CH = C),7. 28-7. 18 (m,4H,ArH), 6. 98-6. 89 (m,1H,CH = CHS),5. 40 (s,2H,CH2O),4. 37 (s,2H,CH2N) ·
[0081] 3-(噻吩-2-基)-4-(2-(2,4-二氯苯基)-2-(2-(4-氟苯基)亚肼基)乙氧基)_1, 5-二氢-2H-吡咯-2-酮(B 9):
[0082] 淡黄色粉末,收率 77. 1%,mp 155. 0-156. 4°C JH NMR(400MHz,DMS0) δ :9· 88 (s, 1Η,ArNH),7· 94(s,1Η,CONH),7· 67(d,J = 2. 0Hz,1Η,ArH),7· 61(d,J = 8. 3Hz,1Η,ArH), 7· 51 (dd,J = 8· 3, 2· 0Hz,1Η,CHS),7· 30 (d,J = 5· 0Hz,1Η,CH = C),7· 20-7. 06 (m,4Η,ArH), 7· 04(d,J = 3· 0Hz,1Η,ArH),6· 85(dd,J = 5· 0,3· 8Hz,1Η,CH = CHS),5· 36(s,2H,CH2O), 4. 26(s,2H,CH2N).
[0083] 3_(噻吩-2-基)-4-(2-苯基-2-(2-(4-溴苯基)亚肼基)乙氧基)-l,5-二 氢-2H-吡咯-2-酮(C 1):
[0084] 浅灰色粉末,收率 71. 2%,mp 139. 2-142. 4°C NMR(400MHz,DMS0) δ :1〇· 16(s, 1H,ArNH),7· 97 (s,1H,CONH),7· 87 (d,J = 7. 5Hz,2H,ArH),7· 50-7. 37 (m,5H,CHS,ArH), 7. 34(d,J = 7. 2Hz,1H,CH = C),7. 31(d,J = 5. 1Hz,lH,ArH),7. 22(d,J = 8. 9Hz,2H,ArH), 6. 92(dd,J = 5. 0,3. 7Hz,1H,CH = CHS),5. 41(s,2H,CH2O),4. 38(s,2H,CH2N).
[0085] 3-(噻吩-2-基)-4-(2-(2-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 2):
[0086] 白色粉末,收率 52. 3%,mp 127. 1-128. 5Γ JH NMR(400MHz,DMS0) δ :9· 95 (s, 1Η,ArNH),7· 93(s,1Η,C0NH),7· 61-7. 54(m,1Η,ArH),7· 50(dd,J = 5· 9,3· 3 Ηζ,1Η,ArH), 7· 41 (dd,J = 8· 9, 5· 9Hz,4Η,CHS,ArH),7· 28 (d,J = 4· 9Hz,1Η,CH = C),7· 11 (d,J = 8· 7Ηζ, 2Η,ArH),7· 03(d,J = 3· 3 Ηζ,1Η,ArH),6· 91-6. 76(m,1Η,CH = CHS),5· 38(s,2H,CH2O), 4. 26(s,2H,CH2N).
[0087] 3_(噻吩-2-基)-4-(2-(2-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 3):
[0088] 白色粉末,收率 35. 6%,mp 152. 2-154. 6°C JH NMR(400MHz,DMS0) δ :9· 92 (s, 1Η,ArNH),7· 93 (s,1Η,CONH),7· 68 (d,J = 7. 8Hz,1Η,ArH),7· 55 (d,J = 7. 1Hz,1Η,CHS), 7. 46(t,J = 7. 4Hz,1H,ArH),7· 40(d,J = 8. 5Hz,2H,ArH),7· 34(t,J = 7. 6Hz,1H,ArH), 7. 28(d,J = 4. 8Hz,1H,CH = C),7. ll(d,J = 8. 5Hz,2H,ArH),7. 02(d,J = 2. 6Hz,lH,ArH), 6. 87-6. 74 (m,1H,CH = CHS),5. 37 (s,2H,CH2O),4. 26 (s,2H,CH2N) ·
[0089] 3-(噻吩-2-基)-4-(2-(3-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 4):
[0090] 淡绿色粉末,收率 37. 6%,mp 126. 2-128. 6°C NMR(400MHz,DMS0) δ :10. 27(s, 1H,ArNH),8· 32(s,1H,CONH),7· 93(d,J = 30. 4Hz,2H,ArH),7· 84(d,J = 7. 7Hz,1H,ArH), 7. 42(dt,J = 14. 1,8. 5Hz,5H,ArH,CHS),7. 32(d,J = 4. 9Hz,1H,CH = C),7. 23(d,J = 8. 7Hz,2H,ArH),7. 01-6. 84(m,1H,CH = CHS),5. 41(s,2H,CH2O),4. 37(s,2H,CH2N).
[0091] 3-(噻吩-2-基)-4- (2- (4-甲氧基苯基)-2- (2- (4-溴苯基)亚肼基)乙氧基)-I, 5-二氢-2H-吡咯-2-酮(C5):
[0092] 白色粉末,收率 55.6%,mp 153.0_155.4°C JH NMR(400MHz,DMS0) δ :l〇.〇3(s, 1H,ArNH),7· 98(s,1H,CONH),7· 81 (d,J = 8. 5Hz,2H,ArH),7· 42 (d,J = 7. 1Hz,3H,CHS, ArH),7. 32 (d,J = 4. 9Hz,1H,CH = C),7. 18 (d,J = 8. 5Hz,2H,ArH),6. 98 (d,J = 8. 5Hz,2H, ArH),6. 95-6. 88 (m,1H,CH = CHS),5. 38 (s,2H,CH2O),4. 37 (s,2H,CH2N),3. 78 (s,3H,OCH3) ·
[0093] 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(C 6):
[0094] 白色粉末,收率 82. 2%,mp 147. 7-148. 6cC JH NMR(400MHz,DMS0) δ :1〇· 05 (s, 1Η,ArNH),7. 97 (s,1Η,CONH),7. 94-7. 84 (m,2Η,ArH),7. 41 (d,J = 2. 6Hz,1Η
当前第3页1 2 3 4 5 
网友询问留言 已有0条留言
  • 还没有人留言评论。精彩留言会获得点赞!
1