Naphtol derivative and process for producing the same

Details Naphtol derivative and process for producing the same Naphtol derivative and process for producing the same

1998-06-05

2000-07-04

Davis, Zinna Northington

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548161, 548190, C07D21375, C07D27503

Patent

active

06084101&

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a novel naphthol derivative which can be used as a raw material for synthesis, such as dyes, pigments, photosensitive materials and the like, and a process for producing the same.


BACKGROUND OF THE INVENTION

The naphthol derivatives is the most economical compounds among the condensed aromatic compounds which forms conjugated polyene systems and has adsorption in the electron band, and is easily used as raw materials for synthesis. Therefore, it has hitherto been used as various characteristic compounds, particularly raw materials such as dyes, pigments, photosensitive materials and the like.
As these naphthol derivatives, there have been known 2-hydroxy-3-phenylaminocarbonylnaphthalene, 2-hydroxy-6-phenylaminocarbonylnaphthalene wherein a substituent is introduced at the 3- or 6-position of 2-hydroxynaphthalene, and those wherein an alkyl or alkoxy group is added to these phenyl groups.
However, only 2-hydroxy-3,6-dihydroxycarbonyl naphthalene has been known as the naphthalene derivatives having substituents at both the 3- and 6-position of 2-hydroxynaphthalene.
An object of the present invention is to provide a novel 3,6-di-substituted-2-hydroxynaphthalene derivative, particularly 2-hydroxy-3,6-dihydroxycarbonylnaphthalene derivative, which is useful as a raw material for synthesis, and a process for producing the same.


DISCLOSURE OF THE INVENTION

The present invention relates to a naphthol derivative represented by the general formula (I): ##STR1## [wherein Y is --(CONH).sub.n --X or --COR, Y' is --(CONH).sub.n --X' or --COR', thiazolyl group, a benzothiazolyl group or a imidazolyl group, and each group may be optionally substituted, optionally branched alkoxy group having 1 to 6 carbon atoms, a halogen atom, a benzyloxy group, a phenyloxy group or a phenacyloxy group, group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms or a phenylalkylene group, hydrogen atom, a halogen atom, a nitro group, a nitroso group or an amino group (Z may be substituted on any ring of the naphthalene ring), and --COR and --COR' respectively], and a process for producing the same.
In particular, the present invention relates to a naphthol derivative represented by the general formula (IV) or (IV'): ##STR2## wherein one of the substituents Y and Y' in the general formula (I) is --(CONH).sub.n --X and the other is --(CONH).sub.n --X or --COR [wherein X, n and R are as defined above].
The naphthol derivative (I) according to the present invention is a novel compound of the naphthol derivative.
The naphthol derivatives (IV) and (IV') according to the present invention are the novel compounds and are compounds wherein an optionally substituted a pyridyl, thiazolyl, benzothiazolyl or imidazolyl group is added at the 3-position and/or 6-position of 2-hydroxynaphthalene through an aminocarbonyl group or --CONHCONH-- group. These residues, which are added through the aminocarbonyl or --CONHCONH-- group, may be same or different at the 3-position and 6-position. The linking groups (aminocarbonyl group and --CONHCONH-- group) may be also the same or different at the 3-position and 6-position.
One of the 3-position and 6-position of the naphthol derivative according to the present invention may be a hydroxycarbonyl group, an optionally branched alkoxycarbonyl group having 1 to 6 carbon atoms, a benzyloxycarbonyl group, a phenyloxycarbonyl group or a phenacyloxycarbbnyl group. The hydrogen atom of the hydroxyl group at the 2-position may be substituted by an alkali metal atom, an optionally branched alkyl group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms or a phenyl-substituted alkylene group. One or more sorts selected from the group consisting of a halogen atom, a nitro group, a nitroso group and an amino group may be introduced into the naphthalene ring.
When X is substituted a pyridyl, thiazolyl, benzothiazolyl or imidazolyl group, the following groups are exemplified as a substituent: alkyl group, alkoxy group, alkyl halide group, ph

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