Naphthol derivatives and process for producing the same

Details Naphthol derivatives and process for producing the same Naphthol derivatives and process for producing the same

1996-12-12

2001-06-26

Shippen, Michael L. (Department: 1621)

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

Organic compounds

Carboxylic acid esters

C548S306400, C548S444000, C552S236000, C552S256000, C560S034000, C560S139000, C560S056000, C562S439000, C562S451000, C562S840000, C564S044000, C564S156000

Reexamination Certificate

active

06252104

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a novel naphthol derivatives which can be used as raw materials etc. for synthesis, such as dyes, pigments, photosensitive materials and the like, and a process for producing the same.
BACKGROUND ART
The naphthol derivatives is the cheapest among condensed aromatic compounds which form a conjugated polyene system and has absorption in the electron band, and is easily used as raw materials for synthesis. Therefore, it has hitherto been used as various peculiar compounds, particularly raw materials such as dyes, pigments, photosensitive materials and the like.
As the naphthol derivatives like this, for example, there have been known 2-hydroxy-3-phenylaminocarbonylnaphthalene or 2-hydroxy-6-phenylaminocarbonylnaphthalene wherein a substituent is introduced at the 3-position or 6-position of 2-hydroxynaphthalene, and those wherein an alkyl or alkoxy group is added to these phenyl groups.
But as the naphthalene derivative which has substituents at both the 3-position and 6-position of 2-hydroxynaphthalene, 2-hydroxy-3,6-dihydroxycarbonylnaphthalene is merely known.
An object of the present invention is to provide novel derivatives of 3,6-di-substituted-2-hydroxynaphthalene, particularly 2-hydroxy-3,6-dihydroxycarbonylnaphthalene, which is useful as raw materials for synthesis, and a process for synthesizing the same.
DISCLOSURE OF THE INVENTION
The present invention relates to naphthol derivatives represented by the general formula (I):
[wherein
Y is —(CONH)
n
—X or —COR;
Y′ is —(CONH)
n
—X′ or —COR′;
X and X′ may be the same or different and indicate a phenyl group, a naphthyl group, an anthraquinonyl group, a benzimidazolonyl group or a carbazolyl group, and each group may be optionally substituted;
R and R′ may be the same or different and indicate a hydroxyl group, an optically branched alkoxy group having 1 to 6 carbon atoms, a halogen atom, a benzyloxy group, a phenyloxy group or a phenacyloxy group;
R
2
is a hydrogen atom, an alkaline metal, an optionally branched alkyl group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms or a phenylalkylene group;
Z indicated one or more sorts of groups selected from the group consisting of a hydrogen atom, a halogen atom, a nitro group, a nitrosos group and an amino group (Z may be substituted on any ring of the naphthalene ring); and
n is an integer of 1 or 2;
provided that R
2
and Z are not simultaneously hydrogen atom when R and R′ simultaneously are hydroxyl group], and a process for producing the same.
Particularly, the present invention relates to naphthol derivatives represented by the general formula (IV)
or (IV′):
wherein one of Y and Y′ is —(CONH)
n
—X and the other is —(CONH)
n
—X or COR in the general formula (I) [X, n and R are as defined above].
More particularly, the present invention relates to naphthol derivatives represented by the general formula (V):
wherein Y and Y′ are respectively represented by COR and COR′ in the general formula (I) [R and R′ are as defined above, provided that R
2
and Z are not simultaneously hydrogen atom when R and R′ simultaneously are hydroxyl group].
The naphthol derivative (I) of the present invention is a novel naphthol derivative compound.
The naphthol derivatives (IV) and (IV′) of the present invention are novel compounds, and are compounds wherein an optionally substituted phenyl, naphthyl, anthraquinonyl, benzimidazolonyl or carbazolyl group is added at the 3-position and/or 6-position of 2-hydroxynaphthalene through an aminocarbonyl or —CONHCONH group. These residues, which are added through the aminocarbonyl or —CONHCONH group, may be the same or different at the 3-position and 6-position. The aminocarbonyl or —CONHCONH group as a coupling group may also be the same or different at the 3-position and 6-position. Regarding the naphthol derivative of the present invention, one of the 3-position and 6-position may be a hydroxycarbonyl group, an optionally branched alkoxycarbonyl group having 1 to 6 carbon atoms, a benzyloxycarbonyl group, a phenyloxycarbonyl group or a phenacyloxycarbonyl group. The hydrogen atom of the hydroxyl group at the 2-position may be substituted with an alkaline 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 a substituted form of the phenyl, naphthyl, anthraquinonyl, benzimidazolonyl or carbazolyl group, examples of the substituent include alkyl group, alkoxy group, alkyl halide group, phenoxy group, alkoxycarbonyl group, nitro group, halogen atom, hydroxyl group, amino group, benzoylamino group, dialkylaminosulfonyl group or cyano group. As the alkyl group, an optionally branched saturated or unsaturated alkyl group having 1 to 6 carbon atoms can be used. Preferred examples thereof include methyl, ethyl, propyl, isopropyl, butyl and t-butyl. As the alkoxy group, an optionally branched saturated or unsaturated alkoxy group having 1 to 6 carbon atoms can be used. Preferred examples thereof include methoxy or ethoxy group. Examples of the halogen atom include fluorine, chlorine, bromine and iodine. The number of the substituent is from 1 to 5, and the substituent may be the same or different.
The naphthol derivative (V) of the present invention is also a novel compound, and a compound wherein a hydroxyl group, a halogen atom, an optionally branched alkoxy group having 1 to 6 carbon atoms, a benzyloxy group, a phenyloxy group or a phenacyloxy group is added at the 3-position and 6-position of 2-hydroxynaphthalene through a carbonyl group. The substituents at the 3-position and 6-position may be the same or different. The hydrogen atom of the hydroxyl group at the 2-position may be substituted with an alkaline 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.
The above naphthol derivative (IV) or (IV′) of the present invention can be produced by condensing a naphthol derivative represented by the general formula (II):
[wherein R
4
is a hydroxyl group or a halogen atom; R
4
′ is a hydroxyl group, a halogen atom or an optionally branched alkoxy group having 1 to 6 carbon atoms; R
5
is a hydrogen atom or a protective group of a hydroxyl group; and Z is as defined above], with an aniline compound represented by the general formula (III):
H
2
N—R
3
—X  (III)
[wherein R
3
is a single bond or —CONH—; provided that X is as defined above].
R
5
in the compound of the formula (II) is a hydrogen atom, an alkaline metal atom or a protective group of a hydroxyl group. The protective group of the hydroxyl group means a group capable of temporarily bonding to a hydroxyl group during the reaction of introducing a substituent into the substitution position which is different from that of the protective group so as to protect the hydroxyl group and then recovering the hydroxyl group easily due to alkaline or acid hydrolysis after the completion of the desirable reaction. Examples thereof include optionally branched alkyl group having 1 to 6 carbon atoms, benzyl group, acetyl group, acetonyl group, tetrahydropyranyl group, trimethylsilyl group and the like.
A phenylurea derivative, wherein R
3
in the compound of the formula (III) is —CONH—, can be obtained by forming an ureido group using a cyanate process of reacting the corresponding aniline compound with cyanic acid.
More specifically, as shown in the reaction scheme (VI):
[wherein A is hydrogen or a suitable substituent], the phenylurea deriv

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