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Volumn , Issue 16, 2008, Pages 2547-2551

Synthesis of 3-fluoro-2,5-disubstituted furans and further derivative reactions to access fluorine-containing 3,3′-bifurans and tetrasubstituted furans

Author keywords

Coupling; Cyclization reaction; DBU; Fluorinated furans; Neighboring group effects

Indexed keywords

3,3' BIFURAN DERIVATIVE; ALCOHOL DERIVATIVE; FLUORINE; FURAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 54149099168     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078053     Document Type: Article
Times cited : (22)

References (46)
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    • Nakanishi, K, Goto, T, Ito, S, Natori, S, Nozoe, S, Eds, Kodansha: Tokyo
    • (b) Natural Products Chemistry, Vol. 1; Nakanishi, K.; Goto, T.; Ito, S.; Natori, S.; Nozoe, S., Eds.; Kodansha: Tokyo, 1974.
    • (1974) Natural Products Chemistry , vol.1
  • 3
    • 0003787448 scopus 로고
    • Nakanishi, K, Goto, T, Ito, S, Natori, S, Nozoe, S, Eds, Kodansha: Tokyo
    • (c) Natural Products Chemistry, Vol. 2; Nakanishi, K.; Goto, T.; Ito, S.; Natori, S.; Nozoe, S., Eds.; Kodansha: Tokyo, 1974.
    • (1974) Natural Products Chemistry , vol.2
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    • 0003787448 scopus 로고
    • Nakanishi, K, Goto, T, Ito, S, Natori, S, Nozoe, S, Eds, Kodansha: Tokyo
    • (d) Natural Products Chemistry, Vol. 3; Nakanishi, K.; Goto, T.; Ito, S.; Natori, S.; Nozoe, S., Eds.; Kodansha: Tokyo, 1974.
    • (1974) Natural Products Chemistry , vol.3
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    • 84943393464 scopus 로고
    • Bird, C. W, Cheeseman, G. W. H, Eds, Pergamon Press: Oxford
    • (e) Sargent, M.; Dean, F. M. In Comprehensive Heterocyclic Chemistry, Vol. 3; Bird, C. W.; Cheeseman, G. W. H., Eds.; Pergamon Press: Oxford, 1984, 599-656.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.3 , pp. 599-656
    • Sargent, M.1    Dean, F.M.2
  • 11
  • 28
    • 34250770967 scopus 로고    scopus 로고
    • For a recent review, see: a
    • For a recent review, see: (a) Schlosser, M.; Mongin, F. Chem. Soc. Rev. 2007, 36, 1161.
    • (2007) Chem. Soc. Rev , vol.36 , pp. 1161
    • Schlosser, M.1    Mongin, F.2
  • 32
    • 54149086861 scopus 로고    scopus 로고
    • Typical Procedure for the Synthesis of 2c from 1c: To a solution of 1c (337 mg, 1 mmol) in anhyd THF (3 mL) was added DBU (3 equiv, 0.45 mL, and the mixture was stirred at 60°C for 8 h. Then the reaction was quenched with H2O (2 mL, and the aqueous layer was extracted with EtOAc. The organic layer was washed with brine and dried over anhyd Na 2SO4. After evaporation of the solvent under reduced pressure, the crude product was purified by column chromatography on silica gel to afford 2c as a white solid (279 mg, 88, 2c: mp 95-96°C. IR: 1631, 1598, 1490, 1430, 1397, 1075, 922, 691 cm-1. 1H NMR (300 MHz, CDCl3, δ, 7.67-7.75 (m, 4 H, 7.10-7.44 (m, 5 H, 6.66 (s, 1 H, 13C NMR (100 MHz, CDCl3, δ, 150.7 (d, 1JCF, 256.0 Hz, 150.5 (d, 3JCF, 8.2 Hz, 134.9 d, 2J CF
    • 10BrFO (315.99): C, 60.59; H, 3.18. Found: C, 60.40; H, 3.37.
  • 35
    • 0038676302 scopus 로고    scopus 로고
    • For examples of the use of the copper(I) Salt-O2 combination in this field, see: (c) Li, X, Hewgley, J. B, Mulrooney, C. A, Yang, J, Kozlowski, M. C. J. Org. Chem. 2003, 68, 5500
    • 2 combination in this field, see: (c) Li, X.; Hewgley, J. B.; Mulrooney, C. A.; Yang, J.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 5500.
  • 42
    • 54149110902 scopus 로고    scopus 로고
    • Typical Procedure for the Synthesis of 3b from 2b: Under an atmosphere of argon, n-butyllithium (0.63 mL, 1.0 mmol) was added dropwise to a stirred solution of 2b (136 mg, 0.5 mmol) in THF (3 mL) at -78°C. Then the reaction mixture was stirred for 40 min at this temperature before CuBr (81 mg, 0.60 mmol) was added and stirred for another 40 min. Then the system was equipped with an oxygen balloon and was allowed to warm to r.t, the reaction solution slowly turned black during this process, After 8 h, 1.0 N HCl (2 mL) was added to quench the reaction and the aqueous layer was extracted with CH2Cl2 and dried over Na2SO 4. The crude product was purified by column chromatography on silica gel to afford 3b as a white solid (64 mg, 47, 3b: mp 177-178°C. IR: 3143, 1636, 1492, 1400, 919, 824, 687 cm-1. 1H NMR (300 MHz, CDCl3, δ, 7.60-7.70 (m, 8 H, 7.42-7.45 m, 4
    • 2: 542.0652; found: 542.0661.
  • 43
    • 54149111083 scopus 로고    scopus 로고
    • Typical Procedure for the Synthesis of 4a from 2a: Under an atmosphere of argon, n-butyllithium (0.38 mL, 0.6 mmol) was added dropwise to a stirred solution of 2a (119 mg, 0.5 mmol) in THF (3 mL) at -78°C. Then the reaction mixture was stirred for 40 min at this temperature before benzaldehyde (64 mg, 0.6 mmol) was added and the system was allowed to warm to r.t. After disappearance of the substrate benzaldehyde (monitored by TLC, the reaction was quenched with sat. NH4Cl. The aqueous layer was extracted with EtOAc and dried over Na2SO4. The crude product was purified by column chromatography on silica gel to afford 4a as a colorless oil (122 mg, 71, 4a: IR: 3366, 3059, 1640, 1495, 1437, 1170, 1015, 839, 693 cm-1. 1H NMR (300 MHz. CDCl 3, δ, 7.54-7.76 (m, 6 H, 7.30-7.44 (m, 9 H, 6.13 (d, J, 6.0 Hz, 1 H, 2.44 (d, J, 6.0 Hz, 1 H, 13C NMR 100
    • 2: 344.1206; found: 344.1213.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.