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Volumn 11, Issue 10, 2009, Pages 2165-2167

Synthesis of 2-substituted 7-hydroxybenzofuran-4-carboxylates via addition of silyl enol ethers to o-benzoquinone esters

Author keywords

[No Author keywords available]

Indexed keywords

2 BENZOQUINONE; 2-BENZOQUINONE; BENZOFURAN DERIVATIVE; BENZOQUINONE DERIVATIVE; CARBOXYLIC ACID; ESTER; ETHER DERIVATIVE; SILANE DERIVATIVE;

EID: 66149128051     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900416x     Document Type: Article
Times cited : (21)

References (27)
  • 7
  • 16
    • 66149117930 scopus 로고    scopus 로고
    • The Diels-Alder reaction of 5, or alkyl analogues, with much less hindered dienes has been reported: (a) Forte, M.; Orsini, F.; Pelizzoni, F.; Ricca, G. Gazz. Chim. Ital. 1985, 115, 41.
    • The Diels-Alder reaction of 5, or alkyl analogues, with much less hindered dienes has been reported: (a) Forte, M.; Orsini, F.; Pelizzoni, F.; Ricca, G. Gazz. Chim. Ital. 1985, 115, 41.
  • 19
    • 33749082314 scopus 로고    scopus 로고
    • Such [4 + 2] cycloadditions are known, as are the simple dimerization of o-benzoquinones. (a) Al-Talib, M.; Gerstenberger, I.; Jones, P. G.; Winterfeldt, E. Liebigs Ann./Recl. 1997, 893.
    • Such [4 + 2] cycloadditions are known, as are the simple dimerization of o-benzoquinones. (a) Al-Talib, M.; Gerstenberger, I.; Jones, P. G.; Winterfeldt, E. Liebigs Ann./Recl. 1997, 893.
  • 25
    • 66149087800 scopus 로고    scopus 로고
    • These compounds were quite difficult to separate and purify by normal silica gel chromatography because of their tendency to adhere to the column, which made elution difficult at times
    • These compounds were quite difficult to separate and purify by normal silica gel chromatography because of their tendency to adhere to the column, which made elution difficult at times.
  • 27
    • 84868939042 scopus 로고    scopus 로고
    • General Procedure for the Oxidation-Cyclization. To a solution of methyl 3,4-dihydroxybenzoate 8 (1.0 mmol) and the silyl enol ether 13 (4 mmol) in 8 mL of THF at 0 °C was added 2 mL (1.1 mmol) of bis(trifluoroacetoxy) iodobenzene (0.55 M solution in THF) dropwise over 10 min, forming a green solution initially. The reaction was allowed to stir at 0 °C (unless specified otherwise) for 4 h, the solution becoming a dark yellow. To the solution was added 0.5 mL of HC1 (4 M solution in dioxane) and 1.0 mL of methanol. The mixture was refluxed for 1 h, and the solution lightened in color. The solution was extracted with 30 mL of diethyl ether, washed with 2 × 10 mL saturated NaHCO3 and 1 × 10 mL brine, dried over MgSO4, filtered, and concentrated in vacuo to yield an oily residue. The residue was purified by flash column chromatography over silica gel (ether and hexanes) to yield the benzofuran product 14. The products were ofte
    • 4, filtered, and concentrated in vacuo to yield an oily residue. The residue was purified by flash column chromatography over silica gel (ether and hexanes) to yield the benzofuran product 14. The products were often recrystallized to give purer material.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.