A direct route to acylhydroquinones from α-keto acids and α- carboxamido acids

Tetrahedron Letters

Volumn 39, Issue 23, 1998, Pages 3957-3960

  Kraus, George A ^a   Melekhov, Alex ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXOACID; ALDEHYDE; BENZOQUINONE; HYDROQUINONE; OXALIC ACID; QUINONE DERIVATIVE;

ARTICLE; CATALYSIS; OXIDATION; PHOTOCHEMISTRY; SYNTHESIS;

EID: 0032482533     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00734-5     Document Type: Article

References (17)

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14. 11. Anhydrous workup of the hydrogenation reaction was essential because of the water solubility of 3.
15. 12. Representative experimental: A solution of amide acid 11 (1 mmol), benzoquinone (5 mmol), ammonium persulfate (1.2 mmol) and silver nitrate (0.2 mmol) in 30 mL of 1:1 acetonitrile:water was heated at 70 °C for 2 hours. The resulting brown solution was diluted with methylene chloride. The organic layer was washed with water and dried over magnesium sulfate. After removal of the solvent in vacuo, the residue was purified by silica gel chromatography using 2:1 hexanes;ethyl acetate to afford 162 mg (62% yield) of quinone 12.
16. 3: 232.0848; measured: 232.0849.
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