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Volumn 11, Issue 22, 2009, Pages 5254-5257

A Pd-Catalyzed heteroannulation approach to 2,3-Disubstituted furo[3,2-c]coumarins

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; PSORALEN DERIVATIVE;

EID: 70749149281     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902189q     Document Type: Article
Times cited : (56)

References (44)
  • 12
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    • A limited number of 3-unsubstituted furo[3,2-è]chromones have been recently reported; see, for instance; (a) Lee, Y. R.; Suk, J. Y. Tetrahedron 2002, 58, 2359.
    • (2002) Tetrahedron , vol.58 , pp. 2359
    • Lee, Y.R.1    Suk, J.Y.2
  • 24
    • 34547603562 scopus 로고    scopus 로고
    • From a synthetic point of view, 2,3-disubstituted furocoumarins have been the focus of recent attention. For leading references, see; (a) Cheng, G.; Hu, Y. Chem. Commun. 2007, 3285.
    • (2007) Chem. Commun. , pp. 3285
    • Cheng, G.1    Hu, Y.2
  • 31
    • 0001658474 scopus 로고
    • In many cases, mixtures of isomeric furo[3,2-c]coumarins and furo[3,2-è]chromones have been previously obtained; see ref 4.
    • (h) Ahluwalia, V. K.; Adhikari, R.; Singh, R. P. Synth. Commun. 1985, 15, 1191. In many cases, mixtures of isomeric furo[3,2-c]coumarins and furo[3,2-è]chromones have been previously obtained; see ref 4.
    • (1985) Synth. Commun. , vol.15 , pp. 1191
    • Ahluwalia, V.K.1    Adhikari, R.2    Singh, R.P.3
  • 32
    • 37049103347 scopus 로고
    • Linear to angular rearrangements have been previously reported, especially in the case of dihydrofuroquinolinones; (a) James, K. J.; Grundon, M. F. J. Chem. Soc., Perkin Trans. 1 1979, 1467.
    • (1979) J. Chem. Soc., Perkin Trans. 1 , pp. 1467
    • James, K.J.1    Grundon, M.F.2
  • 35
    • 0032956647 scopus 로고    scopus 로고
    • The rearrangement of dihydrofurochromones to thermodynamically more stable dihydrofurocoumarins has also been documented
    • (d) Pirrung, M. C.; Blume, F. J. Org. Chem. 1999, 64, 3642. The rearrangement of dihydrofurochromones to thermodynamically more stable dihydrofurocoumarins has also been documented,
    • (1999) J. Org. Chem. , vol.64 , pp. 3642
    • Pirrung, M.C.1    Blume, F.2
  • 37
    • 70749116730 scopus 로고    scopus 로고
    • The formation of the putative furochromenylium salt intermediate could not be observed under these conditions probably due to low stability.
    • The formation of the putative furochromenylium salt intermediate could not be observed under these conditions probably due to low stability.
  • 38
    • 33947458943 scopus 로고
    • 2 to the triple bond at room temperature. However, formation of the desired iodofuran was found to occur at higher temperatures, suggesting that this addition reaction may then become reversible; This process is currently under investigation and details will be reported in a forthcoming paper.
    • 2 to the triple bond at room temperature. However, formation of the desired iodofuran was found to occur at higher temperatures, suggesting that this addition reaction may then become reversible; Miller, S. I.; Noyes, R. M. J. Am. Chem. Soc. 1952, 74, 3403. This process is currently under investigation and details will be reported in a forthcoming paper.
    • (1952) J. Am. Chem. Soc. , vol.74 , pp. 3403
    • Miller, S.I.1    Noyes, R.M.2
  • 39
    • 70749127684 scopus 로고    scopus 로고
    • II salts.
    • II salts.
  • 40
    • 4644262961 scopus 로고
    • Ring-opening processes have already been observed in the case of 3-lithiobenzofurans and 3-lithiofuropyridines; see, respectively; (a) and references therein
    • Ring-opening processes have already been observed in the case of 3-lithiobenzofurans and 3-lithiofuropyridines; see, respectively; (a) Barton, T. J.; Groh, B.L. J. Org. Chem. 1985, 50, 158, and references therein,
    • (1985) J. Org. Chem. , vol.50 , pp. 158
    • Barton, T.J.1    Groh, B.L.2
  • 43
    • 0342728041 scopus 로고
    • 1H NMR). It is likely that 12 resulted from ring-opening of 3-lithiofurochromone 10 leading to enolate intermediate 11 which then underwent anionic cyclization as previously observed (see ref 5a). Equation Found....
    • 1H NMR). It is likely that 12 resulted from ring-opening of 3-lithiofurochromone 10 leading to enolate intermediate 11 which then underwent anionic cyclization as previously observed (see ref 5a). Equation Found....
    • (1981) J. Org. Chem. , vol.46 , pp. 3132
    • Frejd, T.1    Karlsson, J.O.2    Gronowitz, S.3
  • 44
    • 70749131262 scopus 로고    scopus 로고
    • Further work will be undertaken to investigate factors that may influence the product distribution in the Suzuki reaction so as to possibly drive this reaction toward the selective formation of the desired linearly fused products. This would also provide additional information concerning the isomerization process.
    • Further work will be undertaken to investigate factors that may influence the product distribution in the Suzuki reaction so as to possibly drive this reaction toward the selective formation of the desired linearly fused products. This would also provide additional information concerning the isomerization process.


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