Formation of 5-Hydroxy-3-methoxy-1,4-naphthoquinone and 8-Hydroxy-4-methoxy-1,2-naphthoquinone from Juglone

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Formation of 5-Hydroxy-3-methoxy-1,4-naphthoquinone and 8-Hydroxy-4-methoxy-1,2-naphthoquinone from Juglone

From the treatment of 5-hydroxy-1,4-naphthoquinone (juglone) with acetic anhydride and H2SO4 followed subsequently by treatment with methanolic HCl, 5-hydroxy-3-methoxy-1,4-naphthoquinone (3-methoxy juglone) and 8-hydroxy-4-methoxy-1,2-naphthoquinone were obtained as products rather than the anticipated product 2,5-dihydroxy-1,4-naphthoquinone (2-hydroxy juglone). The reaction and the identific...

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SYNTHESIS OF 8-HYDROXY-6-METHOXY- 3-UNDECYLISOCOUMARIN AND 2-HY DROXY - 4-METHOXY-6-(2-OXOTRIDECYL) BENZOIC ACID

Straightforward conversion of (+)-6,8-dimethoxy-3,4-dihydro-3- undecylisocoumarin (3) to the title isocoumarin was carried out. Hydrolytic ring opening of (3) afforded the hydroxy acid (4) which was immediately oxidized to keto acid (5) using chromic acid, Cyclodehydration of (5) afforded the 6,8- dimethoxy-3-undecylisocoumarin (6) which on selective demethylation of 8- methoxy group furni...

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Determination of Juglone (5-hydroxy 1,4-naphthoquinone) in Pterocarya fraxinifolia by RP-HPLC

A method for determination of juglone in leaves and hulls of Pterocarya fraxinifolia was developed, based on RP-HPLC. This compound was extracted from leaves and hulls by chloroform refluxing about 2 hours. The chloroform was evaporated under low pressure at   50 ºC to produce a dry residue. The remained materials were dissolved in acetonitrile to be used for determination of this compound....

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Synthesis of gefitinib from methyl 3-hydroxy-4-methoxy-benzoate.

This paper reports a novel synthesis of gefitinib starting from methyl 3-hydroxy-4-methoxybenzoate. The process starts with alkylation of the starting material, followed by nitration, reduction, cyclization, chlorination and two successive amination reactions. The intermediates and target molecule were characterized by 1H-NMR, 13C-NMR, MS and the purities of all these compounds were determined ...

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synthesis of 8-hydroxy-6-methoxy- 3-undecylisocoumarin and 2-hy droxy - 4-methoxy-6-(2-oxotridecyl) benzoic acid

straightforward conversion of (+)-6,8-dimethoxy-3,4-dihydro-3- undecylisocoumarin (3) to the title isocoumarin was carried out. hydrolytic ring opening of (3) afforded the hydroxy acid (4) which was immediately oxidized to keto acid (5) using chromic acid, cyclodehydration of (5) afforded the 6,8- dimethoxy-3-undecylisocoumarin (6) which on selective demethylation of 8- methoxy group furnished ...

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ژورنال

عنوان ژورنال: ISRN Organic Chemistry

سال: 2012

ISSN: 2090-5157

DOI: 10.5402/2012/274980