Citation: Dao-Lin Wang, Yong-Yang Wang, Xiao-Ce Shi, Jian Ma. An efficient synthesis of novel benzo[b]pyrido[3',2':4,5] thieno[2,3-e][1,6]naphthy-ridine-8-ones[J]. Chinese Chemical Letters, ;2015, 26(9): 1109-1112. doi: 10.1016/j.cclet.2015.05.009 shu

An efficient synthesis of novel benzo[b]pyrido[3',2':4,5] thieno[2,3-e][1,6]naphthy-ridine-8-ones

1.
College of Chemistry and Chemical Engineering, Liaoning Key Laboratory of Synthesis and Application of Functional Compound, Bohai University, Jinzhou 121003, China

Corresponding author: Dao-Lin Wang,
Received Date: 5 March 2015
Available Online: 27 April 2015

An efficient method for the synthesis of novel benzo[b]pyrido[3',2':4,5] thieno[2,3-e][1,6] naphthyridine-8-one derivatives has been developed using a Pictet-Spengler reaction between 4-(3-aminothieno[2,3-b]pyridin-2-yl)quinoline-2-ones, which could be obtained from the alkylation of 4-bromomethylquinoline-2-ones with 3-cyanopyridine-2-thione followed by a Thorpe-Ziegler isomerization, and aromatic aldehydes under p-TsOH as catalysis in good yields.
- 4-Bromomethylquinoline-2-one,
- 3-Cyanopyridine-2-thione,
- Benzo[b]pyrido[3',2':4,5]thieno[2,3-e][1,6],
- naphthyridine-8-one,
- Thorpe-Ziegler reaction,
- Pictet-Spengler reaction
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  [18] Physical and spectral (IR, NMR, Anal.) data:. 5a:Mp > 300℃. IR (KBr, cm^-1):ν 1675(C=O). ¹H NMR (400 MHz, CF₃CO₂D):δ 3.78(s, 3H), 7.55-7.62(m, 7H), 7.79-7.80(m, 2H), 8.81-8.83(m, 2H), 8.98-8.90(m, 1H). ¹³C NMR (100MHz, CF₃CO₂D):δ 30.4, 115.1, 117.5, 117.6, 120.7, 122.8, 124.6, 127.5, 127.8, 127.9, 128.1, 128.4, 131.9, 132.1, 138.5, 139.9, 143.4, 150.3, 151.1, 160.1, 160.9, 162.4. Anal. Calcd. for C₂₄H₁₅N₃OS:C 73.26, H 3.84, N 10.68, S 8.15. Found:C 73.38, H 3.97, N 10.84, S 8.34; 5b:Mp > 300℃. IR (KBr, cm^-1):ν 1685(C=O). ¹H NMR (400 MHz, CF₃CO₂D):δ 2.45(s, 3H), 3.73(s, 3H), 7.32(d, J=7.6 Hz, 2H), 7.51(d, J=7.6 Hz, 2H), 7.52-7.56(m, 3H), 7.74(t, J=8.0 Hz, 1H), 8.80-8.82(m, 2H), 8.89(d, J=8.0 Hz, 1H). ¹³C NMR (100 MHz, CF₃CO₂D):δ 29.7, 30.6, 114.5, 115.9, 117.6, 120.0, 121.5, 122.2, 123.6, 126.8, 127.2, 127.7, 128.2, 129.1, 129.4, 131.4, 131.7, 133.3, 138.6, 149.8, 151.4, 160.1, 161.1. Anal. Calcd. for C₂₅H₁₇N₃OS:C 73.69, H 4.21, N 10.31, S 7.87. Found:C 73.86, H 4.43, N 10.40, S 7.96; 5c:Mp> 300℃. IR (KBr, cm^-1):ν 1676(C=O). ¹H NMR (400 MHz, CF₃CO₂D):δ 3.91(s, 3H), 4.01(s, 3H), 7.23(d, J=8.0 Hz, 1H), 7.33-7.36(m, 2H), 7.61(t, J=8.0 Hz, 1H), 7.86-7.92(m, 2H), 8.16(t, J=8.0Hz, 1H), 8.34-8.35(m, 1H), 8.96(d, J=9.6 Hz, 1H), 9.37-9.38(m, 1H), 9.88(d, J=8.0 Hz, 1H). ¹³C NMR (100 MHz, CF₃CO₂D):δ 31.3, 54.6, 111.2, 113.2, 114.4, 115.0, 116.0, 116.8, 117.8, 118.6, 112.0, 123.7, 124.9, 126.6, 128.1, 129.4, 131.3, 133.3, 137.6, 141.4, 141.8, 145.4, 146.2, 153.8, 158.4. Anal. Calcd. for C₂₅H₁₇N₃O₂S:C 70.90, H 4.05, N 9.92, S 7.57. Found:C 71.04, H 4.14, N 10.08, S 7.64; 5d:Mp> 300℃. IR (KBr, cm^-1):ν 1685(C=O). ¹H NMR (400MHz, CF₃CO₂D):δ 4.22(s, 3H), 4.32(s, 3H), 7.51-7.53(m, 2H), 7.94-7.95(m, 2H), 8.16-8.21(m, 2H), 8.45-8.46(m, 1H), 8.67-8.68(m, 1H), 9.21-9.22(m 1H), 9.66-9.67(m, 1H), 10.21-10.22(m, 1H). ¹³C NMR (100MHz, CF₃CO₂D):δ 31.3, 55.2, 114.9, 115.3, 115.6, 117.2, 124.1, 124.9, 126.2, 127.0, 128.2, 129.1, 130.6, 137.6, 137.9, 141.7, 142.3, 146.5, 146.7, 153.9, 159.2, 159.6, 162.8. Anal. Calcd. for C₂₅H₁₇N₃O₂S:C 70.90, H 4.05, N 9.92, S 7.57. Found:C 70.98, H 4.17, N 10.05, S 7.68; 5e:Mp > 300℃. IR (KBr, cm^-1):ν 1686(C=O). ¹H NMR (400 MHz, CF₃CO₂D):δ 3.92(s, 3H), 7.57-7.62(m, 4H), 7.91-7.93(m, 2H), 8.17-8.19(m, 1H), 8.36-8.37(m, 1H), 8.97-8.99(m, 1H), 9.38-9.39(m, 1H), 9.88-9.89(m, 1H). ¹³C NMR (100MHz, CF₃CO₂D):δ 31.1, 115.2, 116.6, 118.5, 125.6, 126.6, 127.3, 128.2, 128.5, 128.8, 129.4, 129.6, 129.9, 130.0, 137.7, 141.4, 145.3, 146.2, 147.4, 153.8, 158.5, 158.8. Anal. Calcd. for C₂₄H₁₄ClN₃OS:C 67.36, H 3.30, N 9.82, S 7.49. Found:C 67.52, H 3.46, N 9.96, S 7.58; 5f:Mp > 300℃. IR (KBr, cm^-1):ν 1675(C=O). 1HNMR (400MHz, CF₃CO₂D):δ 3.89(s, 3H), 7.29-7.31(m, 2H), 7.62-7.64(m, 2H), 7.86-7.90(m, 2H), 8.14-8.15(m, 1H), 8.34-8.36(m, 1H), 8.93(d, J=7.6Hz, 1H), 9.35-9.36(m, 1H), 9.87(d, J=7.6 Hz, 1H). ¹³C NMR (100 MHz, CF₃CO₂D):δ 30.5, 114.7, 114.9, 115.2, 117.4, 117.6, 120.8, 122.9, 127.5, 128.0, 130.3, 130.4, 132.0, 138.7, 139.9, 150.4, 151.2, 159.8, 160.1, 161.4, 162.1, 163.9. Anal. Calcd. for C₂₄H₁₄FN₃OS:C 70.06, H 3.43, N 10.21, S 7.79. Found:C 70.18, H 3.59, N 10.38, S 7.85; 5g:Mp> 300℃. IR (KBr, cm^-1):ν 1677(C=O). ¹H NMR (400MHz, CF₃CO₂D):δ 3.72(s, 3H), 4.08(s, 3H), 7.35-7.37(m, 1H), 7.45-7.52(m, 4H), 7.60-7.61(m, 3H), 8.32(s, 1H), 8.84-8.86(m, 1H), 8.93(d, J=7.6 Hz,1H). ¹³CNMR(100MHz, CF₃CO₂D):δ 30.6, 55.9, 110.1, 116.4, 117.8, 118.1, 120.0, 120.7, 124.4, 128.3, 128.4, 128.6, 132.2, 134.3, 137.7, 138.3, 140.5, 150.1, 150.9, 155.2, 159.7, 161.2, 162.0. Anal. Calcd. for C₂₅H₁₇N₃O₂S:C 70.90, H 4.05, N 9.92, S 7.57. Found:C 71.04, H 4.18, N 10.05, S 7.69; 5h:Mp > 300℃. IR (KBr, cm^-1):ν 1686(C=O). ¹H NMR (400 MHz, CDCl3):δ 2.45(s, 3H), 3.75(s, 3H), 4.08(s, 3H), 7.33(d, J=8.0 Hz, 2H), 7.45-7.47(m, 3H), 7.52(d, J=9.2 Hz, 1H), 7.76-7.78(m, 1H), 8.26(s, 1H), 8.95-8.96(m, 1H), 9.19(d, J=7.6 Hz, 1H). ¹³CNMR (100MHz, CF₃CO₂D):δ 21.6, 30.6, 55.9, 110.0, 116.3, 117.7, 118.1, 120.0, 120.7, 124.3, 128.2, 128.4, 128.6, 132.0, 134.2, 137.7, 138.2, 140.5, 150.2, 151.0, 155.2, 159.7, 161.1, 162.2. Anal. Calcd. for C₂₆H₁₉N₃O₂S:C 71.38, H 4.38, N 9.60, S 7.33. Found:C 71.47, H 4.53, N 9.74, S 7.48; 5i:Mp > 300℃. IR (KBr, cm^-1):ν 1688(C=O). ¹H NMR (400 MHz, CF₃CO₂D):δ 3.75(s, 3H), 3.89(s, 3H), 4.06(s, 3H), 7.03-7.05(m, 2H), 7.33-7.35(m, 1H), 7.46-7.47(m, 1H), 7.59-7.61(m, 3H), 8.29(s, 1H), 8.33-8.45(m, 1H), 8.94-8.96(m, 1H). ¹³C NMR (100 MHz, CF₃CO₂D):δ 30.5, 55.3, 55.9, 110.1, 113.3, 114.0, 116.4, 117.8, 118.1, 120.0, 120.8, 121.1, 124.6, 128.1, 128.7, 132.1, 134.3, 138.1, 144.7, 150.1, 151.1, 155.2, 159.1, 159.5, 160.8, 162.1. Anal. Calcd. for C₂₆H₁₉N₃O₃S:C 68.86, H 4.22, N 9.27, S 7.07. Found:C 68.98, H 4.37, N 9.41, S 7.16; 5j:Mp > 300℃. IR (KBr, cm^-1):ν 1680(C=O). ¹H NMR (400MHz, CDCl3):δ 3.73(s, 3H), 3.90(s, 3H), 4.09(s, 3H), 7.49-7.55(m, 5H),7.59-7.61(m, 2H), 7.75(t, J=8.0 Hz, 1H), 8.81-8.83(m, 2H), 8.87(d, J=8.0 Hz, 1H). ¹³C NMR (100 MHz, CF₃CO₂D):δ 30.7, 55.3, 56.0, 110.1, 113.3, 116.4, 117.6, 118.2, 120.0, 120.8, 124.2, 128.2, 130.2, 132.1, 134.2, 135.6, 138.4, 150.1, 151.0, 155.2, 159.6, 159.8, 160.7, 162.1. Anal. Calcd. for C₂₆H₁₉N₃O₃S:C 68.86, H 4.22, N 9.27, S 7.07. Found:C 69.02, H 4.35, N 9.43, S 7.19; 5k:Mp > 300℃. IR (KBr, cm^-1):ν 1677(C=O). ¹H NMR (400 MHz, CF₃CO₂D):δ 3.74(s, 3H), 4.07(s, 3H), 7.37(d, J=8.8 Hz, 1H), 7.47-7.49(m, 3H),7.55-7.57(m, 3H), 8.30(s, 1H), 8.85-8.86(m, 1H), 8.90-8.92(m, 1H). ¹³CNMR(100 MHz, CF₃CO₂D):δ 30.6, 56.0, 110.2, 116.5, 117.3, 118.1, 120.0, 120.9, 124.9, 128.0, 128.2, 129.9, 132.3, 134.0, 134.2, 138.4, 141.7, 151.1, 150.9, 155.4, 159.6, 159.9, 161.9. Anal. Calcd. for C₂₅H₁₆ClN₃O₂S:C 65.57, H 3.52, N 9.18, S 7.00. Found:C 65.72, H 3.64, N 9.31, S 7.13; 5l:Mp > 300℃. IR (KBr, cm^-1):ν 1685(C=O). ¹H NMR (400 MHz, CF₃CO₂D):δ 3.74(s, 3H), 4.06(s, 3H), 7.20(m, 2H), 7.37-7.39(m, 1H), 7.47-7.49(m, 1H), 8.60-8.62(m, 3H), 8.30(s, 1H), 8.85-8.86(m, 1H), 7.96-7.98(m, 1H). ¹³C NMR (100 MHz, CF₃CO₂D):δ 30.6, 56.0, 110.1, 114.7, 114.9, 116.5, 118.1, 120.2, 120.9, 124.7, 128.1, 130.3, 130.4, 132.1, 134.2, 136.9, 138.4, 151.2, 155.3, 156.3, 159.7, 159.9, 162.2. Anal. Calcd. for C₂₅H₁₆FN₃O₂S:C 68.01, H 3.65, N 9.52, S 7.26. 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沈阳化工大学材料科学与工程学院沈阳 110142