1987
DOI: 10.1002/chin.198752206
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ChemInform Abstract: Synthesis of Oxygenated Coumestans.

Abstract: The polyhydroxy‐3‐arylcoumarins (I) are dehydrated in methanolic hydrogen chloride or by treatment with sodium acetate/potassium ferricyanide to form the coumestans (II).

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“…The 4-hydroxy-2-oxo-2H-chromen-3-yl group is an organic unit commonly found in natural products as well as in compounds that are synthesized for their biological activities. The C atom at the 3-position of 4-hydroxycoumarin is acidic, and the compound is capable of undergoing a Michael addition across the carbon-carbon double bond of p-benzoquinone (Rani & Darbarwar, 1987). When the reaction is performed in the presence of pyridine, the product is a 1,4dihydroxybenzene whose 2-position bears the chromen-3-yl substituent; as there is a pyridinium group in the 3-position, the compound is a zwitterionic inner salt (Zhang et al, 2004).…”
Section: Commentmentioning
confidence: 99%
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“…The 4-hydroxy-2-oxo-2H-chromen-3-yl group is an organic unit commonly found in natural products as well as in compounds that are synthesized for their biological activities. The C atom at the 3-position of 4-hydroxycoumarin is acidic, and the compound is capable of undergoing a Michael addition across the carbon-carbon double bond of p-benzoquinone (Rani & Darbarwar, 1987). When the reaction is performed in the presence of pyridine, the product is a 1,4dihydroxybenzene whose 2-position bears the chromen-3-yl substituent; as there is a pyridinium group in the 3-position, the compound is a zwitterionic inner salt (Zhang et al, 2004).…”
Section: Commentmentioning
confidence: 99%
“…When the reaction is performed in the presence of pyridine, the product is a 1,4dihydroxybenzene whose 2-position bears the chromen-3-yl substituent; as there is a pyridinium group in the 3-position, the compound is a zwitterionic inner salt (Zhang et al, 2004). For the reaction of 4,7-dihydroxycoumarin and p-benzoquinone, the product is not a disubstituted p-benzoquinone as postulated (Rani & Darbarwar, 1987), but is a disubstituted pdihydroxyphenol. The compound crystallizes from dimethylformamide (DMF) as a trisolvate, (I) (Fig.…”
Section: Commentmentioning
confidence: 99%