Citation: Dao-Lin Wang, Jian-Ying Wu, Qing-Tao Cui. An efficient one-pot synthesis of thiophene-fused pyrido[3,2-a]azulenes via Gewald reaction[J]. Chinese Chemical Letters, ;2014, 25(12): 1591-1594. doi: 10.1016/j.cclet.2014.07.007 shu

An efficient one-pot synthesis of thiophene-fused pyrido[3,2-a]azulenes via Gewald reaction

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: 19 May 2014
Available Online: 1 July 2014
Fund Project:

A simple and efficient procedure was developed for the synthesis of 11H(2H)-4-oxothiophene[3',4':6,5]pyrido[3,2-a]azulene-10-carboxylates (3) in moderate to good yields via the Gewald reaction of ethyl 1-cyanoacetyl-2-methoxyazulene-3-carboxylate (1) with carbonyl compounds (2) and elemental sulfur utilizing imidazole as catalyst. This reaction provides a new procedure for synthesis of pyridinone-fused azulenes.
- Azulene,
- Thiophene,
- Pyridinone,
- Gewald reaction
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  [16] Physical and spectral (IR, NMR, Anal.) data: 3a:Mp 110-112 ℃. IR (KBr, cm^-1): ν 3423 (NH), 1674 (C5O), 1658 (C5O). ¹H NMR (400 MHz, CDCl₃): δ 1.58 (t, 3H, J = 7.2 Hz), 2.36 (s, 3H), 4.55 (q, 2H, J = 7.2 Hz), 7.54 (s, 1H), 7.80-7.87 (m, 3H), 9.46 (d, 1H, J = 10.4 Hz), 10.22 (d, 1H, J = 10.0 Hz), 11.32 (s, 1H). ¹³C NMR (100 MHz, CDCl₃): δ 16.1, 27.2, 60.4, 101.3, 112.3, 117.5, 127.8, 131.9, 133.7, 135.2, 135.8, 137.3, 137.6, 142.3, 144.4, 145.5, 150.7, 165.2, 172.5. Anal. Calcd. for C₁₉H₁₅NO₃S: C 67.64, H 4.48, N 4.15, S 9.50; Found: C 67.79, H 4.64, N 4.27, S 9.61. 3b: Mp 96-98 ℃. IR (KBr, cm^-1): ν 3414 (NH), 1684 (C5O), 1653 (C5O). ¹H NMR (400 MHz, CDCl₃): δ 1.37 (t, 6H, J = 7.2 Hz), 1.55 (t, 3H, J = 7.2 Hz), 2.88 (q, 2H, J = 7.2 Hz), 4.56 (q, 2H, J = 7.2 Hz), 7.51 (s, 1H), 7.81-7.90 (m, 3H), 9.43 (d, 1H, J = 10.4 Hz), 10.20 (d, 1H, J = 10.0 Hz), 11.36 (s, 1H). ¹³C NMR (100 MHz, CDCl₃): δ 14.6, 15.2, 25.6, 60.7, 100.2, 112.1, 118.6, 127.7, 132.6, 133.4, 135.7, 135.9, 137.3, 137.9, 142.0, 144.4, 145.7, 150.5, 165.5, 172.8. Anal. Calcd. for C₂₀H₁₇NO₃S: C 68.36, H 4.88, N 3.99, S 9.12; Found: C 68.45, H 4.95, N 4.16, S 9.24. 3c: Mp 165-167 ℃. IR (KBr, cm^-1): ν 3424 (NH), 1682 (C5O), 1658 (C5O). 1H NMR(400 MHz, CDCl₃): δ 1.01 (t, 3H, J = 3.6 Hz), 1.53 (t, 3H, J = 7.2 Hz), 1.72-1.77 (m, 2H), 2.80-2.83 (m, 2H), 4.55 (q, 2H, J = 7.2 Hz), 7.41 (s, 1H), 7.78-7.81 (m, 1H), 7.85-7.88 (m, 2H), 9.41 (d, 1H, J = 10.0 Hz), 10.20 (d, 1H, J = 9.2 Hz), 11.53 (s, 1H). ¹³C NMR (100 MHz, CDCl₃): δ 13.6, 14.7, 24.2, 32.3, 60.6, 100.1, 112.2, 119.3, 127.8, 132.2, 133.3, 135.6, 136.1, 136.8, 137.1, 142.1, 144.2, 146.6, 150.6, 166.4, 173.5. Anal. Calcd. for C₂₁H₁₉NO₃S: C 69.02, H 5.24, N 3.83, S 8.77; Found: C 69.19, H 5.34, N 3.95, S 8.89. 3d:Mp 174-176 ℃. IR (KBr, cm^-1): ν 3435 (NH), 1689 (C5O), 1643 (C5O). ¹H NMR (400 MHz, CDCl₃): δ 1.38 (d, 6H, J = 6.8 Hz), 1.54 (t, 3H, J = 6.8 Hz), 3.17-3.20 (m, 1H), 4.56 (q, 2H, J = 6.8 Hz), 7.46 (s, 1H), 7.80-7.87 (m, 3H), 9.42 (d, 1H, J = 10.0 Hz), 10.21 (d, 1H, J = 10.0 Hz), 11.57 (s, 1H). ¹³C NMR (100 MHz, CDCl₃): δ 14.7, 34.4, 36.1, 60.6, 100.1, 112.3, 117.1, 127.8, 132.4, 133.3, 135.6, 135.8, 137.2, 142.8, 143.6, 144.2, 145.4, 150.6, 166.2, 173.3. Anal. Calcd. for C₂₁H₁₉NO₃S: C 69.02, H 5.24, N 3.83, S 8.77; Found: C 69.13, H 5.36, N 3.98, S 8.84. 3e:Mp 138-139 ℃. IR (KBr, cm^-1): ν 3483 (NH), 1692 (C5O), 1664 (C5O). ¹H NMR (400 MHz, CDCl₃): δ 0.94 (t, 3H, J = 3.6 Hz), 1.40-1.45 (m, 2H), 1.55 (t, 3H, J = 7.2 Hz), 1.67-1.73 (m, 2H), 2.83-2.87 (m, 2H), 4.56 (q, 2H, J = 7.2 Hz), 7.47 (s, 1H), 7.81-7.89 (m, 3H), 9.43 (d, 1H, J = 10.0 Hz), 10.22 (d, 1H, J = 10.4 Hz), 11.51 (s, 1H). ¹³CNMR(100 MHz, CDCl₃): δ 13.8, 14.7, 22.0, 29.9, 32.2, 60.7, 100.1, 112.2, 119.2, 127.7, 132.5, 133.4, 135.5, 136.5, 136.9, 137.3, 142.1, 144.3, 146.7, 150.6, 166.4, 172.8. Anal. Calcd. for C₂₂H₂₁NO₃S: C 69.63, H 5.58, N 3.69, S 8.45; Found: C 69.78, H 5.76, N 3.83, S 8.56. 3f:Mp 127-129 ℃. IR (KBr, cm^-1): ν 3433 (NH), 1687 (C5O), 1659 (C5O). ¹H NMR (400 MHz, CDCl₃): δ 0.89 (t, 3H, J = 3.6 Hz), 1.36-1.38 (m, 4H), 1.53 (t, 3H, J = 6.8 Hz), 1.72-1.73 (m, 2H), 2.81-2.83 (m, 2H), 4.54 (q, 2H, J = 6.8 Hz), 7.39 (s, 1H), 7.80-7.87 (m, 3H), 9.40 (d, 1H, J = 10.0 Hz), 10.20 (d, 1H, J = 10.4 Hz), 11.54 (s, 1H). ¹³C NMR (100 MHz, CDCl₃): δ 14.0, 14.6, 22.4, 30.2, 30.8, 31.2, 60.7, 100.1, 112.2, 120.2, 127.8, 132.3, 133.2, 135.6, 136.4, 136.7, 137.1, 142.0, 144.1, 146.6, 150.5, 166.6, 173.3. Anal. Calcd. for C₂₃H₂₃NO₃S: C 70.20, H 5.89, N 3.56, S, 8.15; Found: C 70.34, H 5.95, N 3.70, S, 8.29. 3g:Mp 125-127 ℃. IR (KBr, cm^-1): ν 3493 (NH), 1695 (C5O), 1643 (C5O). ¹H NMR (400 MHz, CDCl₃): δ 0.88 (t, 3H, J = 3.6 Hz), 1.30-1.39 (m, 6H), 1.53 (t, 3H, J = 6.8 Hz), 1.69-1.73 (m, 2H), 2.81-2.85 (m, 2H), 4.55 (q, 2H, J = 6.8 Hz), 7.39 (s, 1H), 7.77-7.85 (m, 3H), 9.40 (d, 1H, J = 10.0 Hz), 10.19 (d, 1H, J = 10.4 Hz), 11.25 (s, 1H). 13CNMR(100 MHz, CDCl₃): δ 9.2, 9.8, 16.7, 23.8, 25.4, 26.2, 26.6, 55.7, 96.2, 107.7, 114.3, 122.9, 127.4, 128.4, 130.6, 131.5, 131.8, 132.2, 137.0, 139.2, 141.7, 146.5, 161.2, 168.1. Anal. Calcd. for C₂₄H₂₅NO₃S: C 70.73, H 6.18, N 3.44, S 7.87; Found: C 70.86, H 6.34, N 3.62, S 7.96. 3h:Mp 118-119 ℃. IR (KBr, cm^-1): ν 3453 (NH), 1689 (C5O), 1644 (C5O). ¹H NMR (400 MHz, CDCl₃): δ 0.86 (t, 3H, J = 3.6 Hz), 1.22-1.37 (m, 8H), 1.53 (t, 3H, J = 6.8 Hz), 1.69-1.71 (m, 2H), 2.81-2.86 (m, 2H), 4.55 (q, 2H, J = 6.8 Hz), 7.38 (s, 1H), 7.80-7.86 (m, 3H), 9.39-9.44 (m, 1H), 10.19 (d, 1H, J = 10.4 Hz), 11.23 (s, 1H). ¹³C NMR (100 MHz, CDCl₃): δ 9.2, 9.8, 17.7, 24.0, 25.3, 26.3, 26.8, 55.3, 96.1, 107.3, 114.3, 123.0, 127.4, 128.4, 130.7, 131.4, 131.8, 132.2, 137.2, 139.3, 141.7, 146.7, 161.4, 168.5. Anal. Calcd. for C₂₅H₂₇NO₃S: C 71.23, H 6.46, N 3.32, S 7.61; Found: C 71.37, H 6.63, N 3.47, S 7.76. 3i:Mp 116-117 ℃. IR (KBr, cm^-1): ν 3423 (NH), 1688 (C5O), 1653 (C5O). ¹H NMR (400 MHz, CDCl₃): δ 0.87 (t, 3H, J = 3.6 Hz), 1.26-1.37 (m, 10H), 1.55 (3 t, H, J = 6.8 Hz), 1.69-1.70 (m, 2H), 2.82-2.84 (m, 2H), 4.55 (q, 2H, J = 6.8 Hz), 7.41 (s, 1H), 7.79-7.86 (m, 3H), 9.48-9.52 (m, 1H), 10.20 (d, 1H, J = 10.4 Hz), 11.26 (s, 1H). ¹³C NMR (100 MHz, CDCl₃): δ 9.2, 9.8, 17.8, 24.1, 24.4, 26.4, 26.8, 26.9, 55.7, 96.2, 107.2, 114.2, 122.8, 127.4, 129.4, 130.8, 131.5, 131.8, 132.2, 137.1, 139.2, 141.7, 146.5, 161.6, 168.4. Anal. Calcd. for C₂₆H₂₉NO₃S: C 71.69, H 6.71, N 3.22, S 7.36; Found: C 71.83, H 6.89, N 3.35, S 7.53. 3j:Mp 115-116 ℃. IR (KBr, cm^-1): ν 3429 (NH), 1684 (C5O), 1664 (C5O). ¹H NMR (400 MHz, CDCl₃): δ 0.85 (t, 3H, J = 6.8 Hz), 1.26-1.38 (m, 12H), 1.52 (t, 3H, J = 6.8 Hz), 1.68-1.71 (m, 2H), 2.82 (q, 2H, J = 7.6 Hz), 4.54 (q, 2H, J = 6.8 Hz), 7.37 (s, 1H), 7.76-7.85 (m, 3H), 9.37-9.42 (m, 1H), 10.19 (d, 1H, J = 9.6 Hz), 11.15 (s, 1H). ¹³CNMR(100 MHz, CDCl₃): δ 9.2, 9.8, 17.8, 24.1, 24.4, 24.5, 24.6, 25.3, 26.3, 26.9, 55.7, 96.1, 107.2, 114.2, 121.9, 127.4, 128.3, 130.5, 131.4, 131.8, 132.2, 137.1, 139.2, 141.6, 146.5, 164.5, 168.6. Anal. Calcd. for C₂₇H₃₁NO₃S: C 72.13, H 6.95, N 3.12, S 7.13; Found: C 72.21, H 7.14, N 3.25, S 7.21. 3k:Mp 126-127 ℃. IR (KBr, cm^-1): ν 3434 (NH), 1691 (C5O), 1649 (C5O). ¹H NMR (400 MHz, CDCl₃): δ 1.56 (t, 3H, J = 6.8 Hz), 4.55 (q, 2H, J = 6.8 Hz), 7.28-7.30 (m, 1H), 7.36-7.40 (m, 2H), 7.60-7.62 (m, 2H), 7.77-7.81 (m, 1H), 7.86-7.22 (m, 3H), 9.40 (d, 1H, J = 10.4 Hz), 10.19-10.20 (m, 1H), 11.02 (s, 1H). ¹³C NMR (100 MHz, CDCl₃): δ 14.7, 60.7, 100.1, 112.2, 118.3, 125.6, 127.7, 129.0, 132.5, 133.4, 133.5, 134.1, 135.9, 136.0, 137.2, 142.0, 144.1, 147.1, 150.6, 166.2, 173.5. Anal. Calcd. for C₂₄H₁₇NO₃S: C 72.16, H 4.29, N 3.51, S 8.03; Found: C 72.28, H 4.45, N 3.67, S 8.19. 3l:Mp 204-206 ℃. IR (KBr, cm^-1): ν 3419 (NH), 1681 (C5O), 1654 (C5O). ¹H NMR (400 MHz, CDCl₃): δ 1.50 (t, 3H, J = 6.8 Hz), 1.75-1.89 (m, 2H), 2.71-2.83 (m, 2H), 3.23-3.31 (m, 2H), 4.53 (q, 2H, J = 6.8 Hz), 7.72-7.85 (m, 3H), 9.36 (d, 1H, J = 10.0 Hz), 10.14-10.19 (m, 1H), 11.13 (s, 1H). ¹³C NMR (100 MHz, CDCl₃): δ 14.6, 27.4, 29.1, 31.0, 59.6, 103.1, 107.3, 114.5, 122.7, 127.9, 128.5, 130.4, 131.0, 131.4, 132.1, 137.6, 140.2, 141.3, 146.0, 164.7, 168.1. Anal. Calcd. for C₂₁H₁₇NO₃S: C 69.40, H 4.71, N 3.85, S 8.82; Found: C 69.56, H 4.82, N 3.96, S 8.98. 3m: Mp 213-215 ℃. IR (KBr, cm^-1): ν 3416 (NH), 1685 (C5O), 1658 (C5O). ¹H NMR (400 MHz, CDCl₃): δ 1.51 (t, 3H, J = 6.8 Hz), 1.80-1.92 (m, 4H), 2.74-2.81 (m, 2H), 3.25-3.34 (m, 2H), 4.52 (q, 2H, J = 6.8 Hz), 7.71-7.82 (m, 3H), 9.34 (d, 1H, J = 10.0 Hz), 10.17-10.20 (m, 1H), 11.10 (s, 1H). ¹³CNMR(100 MHz, CDCl₃): δ 14.7, 23.0, 23.4, 24.7, 27.1, 59.7, 105.1, 108.2, 113.8, 122.1, 127.6, 128.6, 130.2, 131.6, 132.0, 132.6, 137.6, 140.2, 141.7, 146.8, 165.4, 168.3. Anal. Calcd. for C₂₂H₁₉NO₃S: C 70.00, H 5.07, N 3.71, S 8.50; Found: C 70.17, H 5.14, N 3.85, S 8.65.
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沈阳化工大学材料科学与工程学院沈阳 110142