Citation: Dao-Lin Wang, Dan Wu, Wei Zhao, Yong-Yang Wang, Jian-Ying Wu. An efficient synthesis of benzo[b]benzofurano[2,3-e]-[1,6]naphthyridine-8-ones[J]. Chinese Chemical Letters, ;2015, 26(2): 251-254. doi: 10.1016/j.cclet.2014.11.005 shu

An efficient synthesis of benzo[b]benzofurano[2,3-e]-[1,6]naphthyridine-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 September 2014
Available Online: 23 October 2014
Fund Project:

An efficient method for the synthesis of benzo[b]benzofurano[2,3-e][1,6]naphthyridine-8-one derivatives has been developed via Pictet-Spengler reaction of 4-(3-aminobenzofuran-2-yl)quinoline- 2-ones, which could be obtained from alkylation of 4-bromomethylquinoline-2-ones with salicylonitrile and subsequent Thorpe-Ziegler isomerization, with aromatic aldehydes under p-TsOH as catalyst in good yields.
- 4-Bromomethylquinoline-2-one,
- Salicylonitrile,
- Benzo[b]benzofurano[2,3-e][1,6]naphthyridine-8-one,
- Thorpe-Ziegler isomerization,
- Pictet-Spengler reaction
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  [17] Physical and spectral (IR, NMR, Anal.) data: 5a: Mp 280-282 8C. IR (KBr, cm^-1): 1680 (C5O). 1H NMR (400 MHz, CDCl₃): 3.69 (s, 3H), 7.42-7.54 (m, 8H), 7.63-7.71 (m, 2H), 7.78 (d, 1H, J=8.4 Hz), 8.37 (d, 1H, J=7.6 Hz), 9.37 (d, 1H, J=8.0 Hz). ¹³C NMR (100 MHz, CDCl₃): 30.3, 112.1, 112.5, 114.5, 114.9, 116.7, 122.7, 123.2, 124.1, 124.6, 127.6, 127.9, 128.1, 128.4, 129.7, 129.9, 131.9, 132.3, 139.9, 143.9, 158.3, 159.2, 159.9. Anal. Calcd. for C₂₅H₁₆N₂O₂: C 79.77, H 4.28, N 7.44. Found: C 79.84, H 4.38, N 7.56; 5b: Mp 284-286 8C. IR (KBr, cm^-1): 1684 (C5O). 1H NMR (400 MHz, CDCl₃): 2.45 (s, 3H), 3.71 (s, 3H), 7.30-7.32 (m, 2H), 7.42-7.50 (m, 5H), 7.64-7.71 (m, 2H), 7.79 (d, 1H, J=8.0 Hz), 8.38 (d, 1H, J=7.6 Hz), 9.38 (d, 1H, J=8.0 Hz). ¹³C NMR (100 MHz, CDCl₃): 21.7, 30.5, 112.1, 112.4, 114.4, 114.9, 115.8, 116.5, 122.2, 122.5, 123.1, 123.9, 124.4, 127.8, 128.3, 128.9, 129.8, 131.7, 132.0, 139.8, 143.6, 158.3, 159.6, 160.2. Anal. Calcd. for C₂₆H₁₈N₂O₂: C 79.98, H 4.65, N 7.17. Found: C 80.15, H 4.79, N 7.26; 5c: Mp 285-287 8C. IR (KBr, cm^-1): 1675 (C5O). 1H NMR (400 MHz, CDCl₃): 3.66 (s, 3H), 3.69 (s, 3H), 6.99-7.01 (m, 1H), 7.14-7.15 (m, 1H), 7.46-7.50 (m, 5H), 7.65-7.67 (m, 2H), 7.79 (d, 1H, J=8.4 Hz), 8.44 (d, 1H, J=7.6 Hz), 8.40 (d, 1H, J=8.0 Hz). ¹³C NMR (100 MHz, CDCl₃): 30.2, 55.4, 110.4, 110.6, 112.0, 112.4, 114.3, 114.8, 118.1, 120.6, 121.0, 122.4, 122.9, 123.8, 124.4, 128.4, 128.9, 129.6, 129.8, 131.6, 131.9, 139.9, 143.9, 156.6, 158.1, 159.9. Anal. Calcd. for C₂₆H₁₈N₂O₃: C 76.83, H 4.46, N 6.89. Found: C 76.94, H 4.58, N 6.96; 5d: Mp 289-290 8C. IR (KBr, cm^-1): 1684 (C5O). 1H NMR (400 MHz, CDCl₃): 3.71 (s, 3H), 3.86 (s, 3H), 7.01 (s, 1H), 7.07 (d, 1H, J=7.6 Hz), 7.40-7.43 (m, 2H), 7.45-7.51 (m, 3H), 7.68-7.71 (m, 2H), 7.80 (d, 1H, J=8.4 Hz), 8.40 (d, 1H, J=7.6 Hz), 9.39 (d, 1H, J=8.0 Hz). ¹³C NMR (100 MHz, CDCl₃): 30.3, 55.3, 113.1, 113.4, 113.9, 114.4, 114.9, 115.8, 116.6, 120.6, 121.0, 122.5, 123.1, 123.9, 124.4, 127.8, 128.5, 129.0, 129.6, 129.8, 130.1, 139.9, 143.7, 158.3, 159.2, 159.9. Anal. Calcd. for C₂₆H₁₈N₂O₃: C 76.83, H 4.46, N 6.89. Found: C 76.96, H 4.57, N 6.99; 5e: Mp 293-295 8C. IR (KBr, cm^-1): 1686 (C5O). 1H NMR (400 MHz, CDCl₃): 3.71 (s, 3H), 3.87 (s, 3H), 7.03 (d, 2H, J=7.6 Hz), 7.62-7.66 (m, 5H), 7.69-7.71 (m, 2H), 7.77 (d, 1H, J=8.4 Hz), 8.38 (d, 1H, J=7.6 Hz), 9.37 (d, 1H, J=8.0 Hz). ¹³C NMR (100 MHz, CDCl₃): 30.3, 55.1, 112.1, 112.4, 113.2, 113.4, 114.4, 114.8, 116.4, 122.4, 122.6, 123.0, 123.9, 124.4, 129.5, 129.8, 130.0, 131.7, 132.0, 139.8, 143.6, 158.3, 159.2, 160.2. Anal. Calcd. for C₂₆H₁₈N₂O₃: C 76.83, H 4.46, N 6.89. Found: C 76.98, H 4.54, N 7.02; 5f:Mp 296-298 8C. IR (KBr, cm^-1): 1673 (C5O). 1H NMR (400 MHz, CDCl₃): 3.73 (s, 3H), 3.93 (s, 3H), 3.95 (s, 3H), 6.98-6.99 (m, 1H), 7.01-7.02 (m, 2H), 7.07-7.08 (m, 3H), 7.09-7.12 (m, 2H), 7.14 (d, 1H, J=7.6 Hz), 8.44 (d, 1H, J=7.6 Hz), 9.40 (d, 1H, J=8.0 Hz). ¹³C NMR (100 MHz, CDCl₃): 30.5, 55.7, 55.9, 110.4, 110.6, 111.7, 112.1, 112.4, 114.4, 114.9, 115.7, 116.5, 121.0, 121.5, 122.6, 123.1, 124.0, 124.5, 129.6, 129.8, 131.9, 132.2, 143.7, 148.4, 158.3, 158.9, 160.0. Anal. Calcd. for C27H20N2O4: C 74.30, H 4.62, N 6.42. Found: C 74.45, H 4.74, N 6.58; 5g: Mp >300℃. IR (KBr, cm^-1): 1675 (C5O). 1H NMR (400 MHz, CDCl₃): 3.67 (s, 3H), 3.74 (s, 3H), 3.93 (s, 3H), 3.97 (s, 3H), 6.64 (s, 1H), 7.11 (s, 1H), 7.46-7.48 (m, 4H), 7.71-7.76 (m, 2H), 7.82-7.84 (m, 1H), 9.43 (d, 1H, J=8.0 Hz). ¹³C NMR (100 MHz, CDCl₃): 30.3, 55.1, 112.1, 112.4, 113.2, 113.4, 114.4, 114.8, 116.4, 122.4, 122.6, 123.0, 123.9, 124.4, 129.5, 129.8, 130.0, 131.7, 132.0, 139.8, 143.6, 158.3, 159.2, 160.2. Anal. Calcd. for C₂₈H₂₂N₂O₅: C 72.09, H 4.75, N 6.01. Found: C 72.14, H 4.83, N 6.13; 5h: Mp >300℃. IR (KBr, cm^-1): 1687 (C5O). 1H NMR (400 MHz, CDCl₃): 3.73 (s, 3H), 7.47-7.53 (m, 7H), 7.66-7.68 (m, 2H), 7.81 (d, 1H, J=8.4 Hz), 8.35 (d, 1H, J=8.0 Hz), 9.40 (d, 1H, J=8.0 Hz). ¹³C NMR (100 MHz, CDCl₃): 30.5, 112.2, 112.5, 112.7, 114.5, 114.9, 120.7, 122.0, 122.3, 122.7, 123.2, 124.0, 127.7, 128.3, 129.4, 129.6, 129.8, 129.9, 144.2, 144.3, 158.2, 158.3, 168.3. Anal. Calcd. for C25H15ClN2O2: C 73.08, H 3.68, N 6.82. Found: C 73.16, H 3.84, N 6.94; 5i: Mp >300℃. IR (KBr, cm^-1): 3410 (NH), 1689 (C5O). 1H NMR (400 MHz, CF₃CO₂D): 7.59-7.68 (m, 5H), 7.71-7.78 (m, 3H), 7.96-8.01 (m, 3H), 8.32 (d, 1H, J=8.4 Hz), 9.57 (d, 1H, J=8.4 Hz). ¹³C NMR (100 MHz, CF₃CO₂D): 112.7, 113.7, 115.1, 115.6, 116.1, 121.0, 121.3, 126.6, 127.0, 127.3, 127.8, 129.1, 129.3, 131.0, 133.9, 134.8, 135.4, 137.1, 145.4, 153.5, 158.5, 159.6. Anal. Calcd. for C24H14N2O2: C 79.55, H 3.89, N 7.73. Found: C 79.67, H 3.95, N 7.89; 5j: Mp >300℃. IR (KBr, cm^-1): 3427 (NH), 1679 (C5O). 1H NMR (400 MHz, CF₃CO₂D): 2.49 (s, 3H), 7.42-7.48 (m, 4H), 7.60 (d, 1H, J=8.0 Hz), 7.77-7.79 (m, 2H), 7.96-8.07 (m, 3H), 8.33 (d, 1H, J=8.0 Hz), 9.57 (d, 1H, J=8.4 Hz). ¹³C NMR (100 MHz, CF₃CO₂D): 18.2, 112.7, 113.7, 114.9, 115.6, 121.0, 121.3, 126.6, 127.2, 127.9, 128.5, 129.1, 129.2, 133.9, 134.8, 134.9, 135.3, 137.1, 142.4, 145.2, 153.8, 158.4, 159.7. Anal. Calcd. for C₂₅H₁₆N₂O₂: C 79.77, H 4.28, N 7.44. Found: C 79.85, H 4.41, N 7.53; 5k: Mp >300℃. IR (KBr, cm^-1): 3415 (NH), 1676 (C5O). 1H NMR (400 MHz, CF₃CO₂D): 4.01 (s, 3H), 7.22 (d, 2H, J=8.0 Hz), 7.58-7.62 (m, 3H), 7.70-7.72 (m, 2H), 7.74-7.78 (m, 3H), 8.33 (d, 1H, J=7.6 Hz), 9.56 (d, 1H, J=8.4 Hz). ¹³C NMR (100 MHz, CF₃CO₂D): 55.1, 113.9, 114.3, 114.8, 122.2, 122.5, 125.5, 126.2, 126.4, 126.5, 126.7, 130.3, 130.4, 130.6, 135.1, 136.0, 136.1, 136.6, 138.3, 146.4, 154.2, 159.6, 160.9. Anal. Calcd. for C25H16N2O3: C 76.52, H 4.11, N 7.14. Found: C 76.63, H 4.27, N 7.28; 5l: Mp >300℃. IR (KBr, cm^-1): 3424 (NH), 1683 (C5O). 1H NMR(400 MHz, CF₃CO₂D): d 7.53-7.73 (m, 5H), 7.50-7.76 (m, 2H), 7.96-8.07 (m, 3H), 8.33 (d, 1H, J=8.0 Hz), 9.56 (d, 1H, J=8.0 Hz). ¹³C NMR (100 MHz, CF₃CO₂D): d 113.5, 114.6, 116.1, 116.6, 122.0, 122.3, 128.6, 128.9, 129.1, 129.4, 130.1, 130.2, 135.0, 135.8, 136.0, 136.4, 138.1, 138.7, 146.4, 153.2, 159.5, 160.4. Anal. Calcd. for C₂₄H₁₃ClN₂O₂: C 72.64, H 3.30, N 7.06. Found: C 72.76, H 3.46, N 7.15.
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沈阳化工大学材料科学与工程学院沈阳 110142