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Citation: Dao-Lin Wang, Zhe Dong, Jiao Xu, Di Li. An efficient synthesis of 2-(guaiazulen-1-yl)furan derivatives via intramolecular Wittig reactions[J]. Chinese Chemical Letters, ;2013, 24(07): 622-624. shu

An efficient synthesis of 2-(guaiazulen-1-yl)furan derivatives via intramolecular Wittig reactions

  • 1.

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

  • 2.

    b Cosmetology Department, Jiamusi Institute, Heilongjiang University of Chinese Medicine, Jiamusi 154007, China

  • Corresponding author: Dao-Lin Wang,  Jiao Xu, 
  • Received Date: 24 January 2013
    Available Online: 9 April 2013

  • An efficient and mild synthesis of 2-(guaiazulen-1-yl)furans, starting from easily accessible 1-(3-aryl-2-cyanopropenoyl)guaiazulenes, tributylphosphine and acyl chlorides, is described. The strategy employs the intramolecular Wittig protocol as a key step to append the crucial furan ring, leading to the highly functional furans in good yields.
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      [11] Physical and spectral data 4a: Mp: 154-156℃; IR (KBr): ν 2208 cm-1 (CN); 1H NMR (400 MHz, CDCl3): δ 1.40 (d, 6H, J=6.9 Hz, CH(CH3)2), 2.66 (s, 3H, CH3), 2.76 (s, 3H, CH3), 3.11-3.16 (m, 1H, CH(CH3)2), 7.18 (d, 1H, J=10.5 Hz), 7.40-7.48 (m, 8H), 7.53-7.56 (m, 3H), 7.90 (s, 1H), 8.29 (s, 1H). Anal. Calcd. for C32H27NO: C 87.04, H 6.16, N 3.17; found: C 87.15, H 6.23, N 3.26. 4b: Mp: 165-167℃; IR (KBr): ν 2213 cm-1 (CN); 1H NMR (400 MHz, CDCl3): δ 1.40 (d, 6H, J=6.9 Hz, CH(CH3)2), 2.40 (s, 3H, CH3), 2.66 (s, 3H, CH3), 2.75 (s, 3H, CH3), 3.10-3.15 (m, 1H, CH(CH3)2), 7.21 (d, 1H, J=10.5 Hz), 7.35-7.48 (m, 7H), 7.50-7.58 (m, 3H), 7.90 (s, 1H), 8.25 (s, 1H). Anal. Calcd. for C33H29NO: C 87.00, H 6.42, N 3.07; found: C 87.16, H 6.51, N 3.14. 4c: Mp: 189-191℃; IR (KBr): ν 2208 cm-1 (CN); 1H NMR (400 MHz, CDCl3): δ 1.41 (d, 6H, J=6.9 Hz, CH(CH3)2), 2.67 (s, 3H, CH3), 2.75 (s, 3H, CH3), 3.11-3.17 (m, 1H, CH(CH3)2), 3.80 (s, 3H, OCH3), 6.81 (d, 2H, J=8.9 Hz), 7.18 (d, 1H, J=10.5 Hz), 7.40-7.48 (m, 5H), 7.51-7.57 (m, 3H), 7.93 (s, 1H), 8.27 (s, 1H). Anal. Calcd. for C33H29NO2: C 84.05, H 6.20, N 2.97; found: C 84.23, H 6.31, N 3.15. 4d: Mp: 171-173℃; IR (KBr): ν 2213 cm-1 (CN); 1H NMR (400 MHz, CDCl3): δ 1.40 (d, 6H, J=6.9 Hz, CH(CH3)2), 2.42 (s, 3H, CH3), 2.66 (s, 3H, CH3), 2.74 (s, 3H, CH3), 3.10-3.15 (m, 1H, CH(CH3)2), 3.79 (s, 3H, OCH3), 6.80 (d, 2H, J=8.7 Hz), 7.18 (d, 1H, J=10.5 Hz), 7.24-7.27 (m, 4H), 7.42-7.47 (m, 4H), 7.52 (d, 1H, J=10.5 Hz), 7.92 (s, 1H), 8.26 (s, 1H). Anal. Calcd. for C34H31NO2: C 84.09, H 6.43, N 2.88; found: C 84.17, H 6.59, N 3.04. 4e: Mp: 161-163℃; IR (KBr): ν 2216 cm-1 (CN); 1H NMR (400 MHz, CDCl3): δ 1.39 (d, 6H, J=6.9 Hz, CH(CH3)2), 2.66 (s, 3H, CH3), 2.74 (s, 3H, CH3), 3.08-3.17 (m, 1H, CH(CH3)2), 3.79 (s, 3H, OCH3), 3.87 (s, 3H, OCH3), 6.81 (d, 2H, J=8.7 Hz), 6.98 (d, 2H, J=8.7 Hz), 7.17 (d, 1H, J=10.8 Hz), 7.44-7.53 (5H, m), 7.92 (s, 1H), 8.27 (s, 1H). Anal. Calcd. for C34H31NO3: C 81.41, H 6.23, N 2.79; found: C 81.58, H 6.41, N 2.96. 4f: Mp: 153-155℃; IR (KBr): ν 2219 cm-1 (CN); 1H NMR (400 MHz, CDCl3): δ 1.38 (d, 6H, J=6.9 Hz, CH(CH3)2), 2.67 (s, 3H, CH3), 2.74 (s, 3H, CH3), 3.11-3.18 (m, 1H, CH(CH3)2), 3.81 (s, 3H, OCH3), 6.82 (d, 2H, J=9.0 Hz), 7.19 (d, 1H, J=10.8 Hz), 7.41-7.44 (m, 5H), 7.50 (d, 2H, J=8.7 Hz), 7.92 (s, 1H), 8.28 (s, 1H). Anal. Calcd. for C33H28ClNO2: C 78.33, H 5.58, N 2.77; found: C 78.47, H 5.73, N 2.89. 4g: Mp: 121-123℃; IR (KBr): ν 2215 cm-1 (CN); 1H NMR (400 MHz, CDCl3): δ 1.37 (d, 6H, J=6.8 Hz, CH(CH3)2), 2.48 (s, 3H, CH3), 2.61 (s, 3H, CH3), 2.85 (s, 3H, CH3), 3.12-3.17 (m, 1H, CH(CH3)2), 6.89 (d, 2H, J=8.0 Hz), 7.29-7.31 (m, 4H), 7.35 (d, 1H, J=10.8 Hz), 7.64 (d, 1H, J=10.8 Hz), 7.88 (s, 1H), 7.95 (d, 2H, J=8.4 Hz), 8.31 (s, 1H). Anal. Calcd. for C33H28N2O3: C 79.18, H 5.64, N 5.60; Found: C 79.34, H 5.79, N 5.81. 4h: Mp: 115-117℃; IR (KBr): ν 2219 cm-1 (CN); 1H NMR (400 MHz, CDCl3): δ 1.37 (d, 6H, J=6.8 Hz, CH(CH3)2), 2.62 (s, 3H, CH3), 2.83 (s, 3H, CH3), 3.11-3.15 (m, 1H, CH(CH3)2), 3.83 (s, 3H, OCH3), 6.91 (d, 2H, J=7.6 Hz), 7.01 (d, 2H, J=8.8 Hz), 7.34 (d, 1H, J=10.8 Hz), 7.30-7.32 (m, 2H), 7.62 (d, 1H, J=10.8 Hz), 7.88 (s, 1H), 8.03 (d, 2H, J=8.8 Hz), 8.30 (s, 1H). Anal. Calcd. for C33H28N2O4: C 76.73, H 5.46, N 5.42; found: C 76.86, H 5.63, N 5.57. 4i: Mp: 139-140℃; IR (KBr): ν 2225 cm-1 (CN); 1H NMR (400 MHz, CDCl3): δ 1.38 (d, 6H, J=6.3 Hz, CH(CH3)2), 2.67 (s, 3H, CH3), 2.71 (s, 3H, CH3), 3.12-3.16 (m, 1H, CH(CH3)2), 3.84 (s, 3H, OCH3), 6.53-6.55 (m, 1H), 6.82-6.83 (m, 1H), 6.91 (d, 2H, J=8.1 Hz), 7.17 (d, 1H, J=9.9 Hz), 7.51 (d, 1H, J=9.9 Hz), 7.53-7.54 (m, 1H), 7.62 (d, 2H, J=8.1 Hz), 7.90 (s, 1H), 8.26 (s, 1H). Anal. Calcd. for C31H27NO3: C 80.67, H 5.90, N 3.03; found: C 80.75, H 6.11, N 3.09. 4j: Mp: 154-156℃; IR (KBr): ν 2218 cm-1 (CN); 1H NMR (400 MHz, CDCl3): δ 1.35 (d, 6H, J=6.8 Hz, CH(CH3)2), 1.53 (s, 3H, CH3), 2.62 (s, 3H, CH3), 2.86 (s, 3H, CH3), 3.13-3.16 (m, 1H, CH(CH3)2), 7.37-7.40 (m, 2H), 7.63-7.65 (m, 5H), 7.89 (s, 1H), 8.32 (s, 1H). Anal. Calcd. for C27H25NO: C 85.45, H 6.64, N 3.69; found: C 85.57, H 6.80, N 3.73. 4k: Mp: 169-171℃; IR (KBr): ν 2215 cm-1 (CN); 1H NMR (400 MHz, CDCl3): δ 1.37 (d, 6H, J=6.8 Hz, CH(CH3)2), 1.54 (s, 3H, CH3), 2.48 (s, 3H, CH3), 2.62 (s, 3H, CH3), 2.86 (s, 3H, CH3), 3.12-3.17 (m, 1H, CH(CH3)2), 7.19 (d, 1H, J=10.8 Hz), 7.20-7.25 (m, 4H), 7.53 (d, 1H, J=10.8 Hz), 7.85 (s, 1H), 8.24 (s, 1H). Anal. Calcd. for C28H27NO: C 85.46, H 6.92, N 3.56; found: C 85.63, H 7.11, N 3.74. 4l: Mp: 135-137℃; IR (KBr): ν 2212 cm-1 (CN); 1H NMR (400 MHz, CDCl3): δ 1.05 (t, 3H, J=7.6 Hz, CH2CH3), 1.38 (d, 6H, J=6.8 Hz, CH(CH3)2), 1.41 (q, 2H, J=7.6 Hz, CH2CH3), 2.62 (3H, s, CH3), 2.85 (3H, s, CH3), 3.12-3.18 (m, 1H, CH(CH3)2), 3.82 (s, 3H, OCH3), 7.19 (d, 1H, J=9.2 Hz), 7.19-7.22 (m, 4H), 7.52 (d, 1H, J=9.2 Hz), 7.85 (s, 1H), 8.24 (s, 1H). Anal. Calcd. for C29H29NO2: C 82.24, H 6.90, N 3.31; found: C 82.38, H 7.03, N 3.47.

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