- A convenient synthesis of 4-alkoxylated isoindolin-1-ones
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A short synthesis of 4-alkoxylated isoindolin-1-ones based upon the S NAr reaction applied to phosphorylated 2-methoxybenzamides followed by alkaline cleavage of the phosphoryl auxiliary is reported.
- Moreau, Anne,Couture, Axel,Deniau, Eric,Grandclaudon, Pierre
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p. 1664 - 1670
(2007/10/03)
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- The Chemistry of 2H-3,1-Benzoxazine-2,4(1H)-dione (Isatoic Anhydride). 21. A Mild Process For The Preparation of 10-Alkyl-9-acridanones And It's Application To The Synthesis of Acridone Alkaloids
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10-Substituted-9-acridanones are readily prepared by the reaction of the corresponding isatoic anhydride with the lithium enolate of 2-cyclohexen-1-one.The initially formed product, the 1,2-dihydroacridone need not be purified but can be aromatized directly with DDQ to the desired acridone.This methodology is applicable to the synthesis of acridone natural products.Two alkaloids, 1,2,3-trimethoxy-10-methylacridone (9) and evoxanthine (10), were prepared from 4,5,6-trimethoxy-N-methylisatoic anhydride and 6-methoxy-4,5-methylenedioxy-N-methylisatoic anhydride respectively.In these trioxygenated systems, palladium-on-charcoal must be used to aromatize the penultimate intermediate.
- Coppola, Gary M.,Schuster, Herbert F.
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p. 957 - 964
(2007/10/02)
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- Synthesis of the Yeast Antioxidant Benzofuran and Analogues
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2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran, the active antioxidant which occurs in yeasts, and related 2-arylbenzofurans have been synthesized by a convergent route.The key step involves benzofuran formation by an intramolecular Wittig reaction.
- McKittrick, Brian A.,Stevenson, Robert
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p. 709 - 712
(2007/10/02)
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