JPH09176158A - Nitrogen-containing heterocyclic compound and its production - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new nitrogen-containing heterocyclic compound high in light absorbance and useful for dyestuffs, additives, medicines, agrochemicals, etc. SOLUTION: This compound is expressed by formula I [R1 -R6 are each H, a substituent; Y1 is O, S, N(R7 ); Y2 is O, S, N(R8 ), C(R9 )(R10 ) (R7 -R10 are each H, an alkyl, an aryl, O); A1 , A2 are each a five or six-membered nitrogen- containing heterocyclic group], for example, a compound of formula III. The compound of formula I is obtained by reacting a compound of formula: A1 -X (X is a releasable group) with a compound of the formula: A2 -X. The compound of formula III is new.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel nitrogen-containing heterocyclic compound, a process for producing the same and a synthetic intermediate.

[0002]

2. Description of the Related Art Nitrogen-containing heterocyclic compounds are not only useful as UV absorbers, dyes, additives, pharmaceuticals, agricultural chemicals, chelating agents, etc., but also various functional compounds (cyanine dyes, dyes, pharmaceuticals, agricultural chemicals). , Functional materials, etc.) are important as synthetic intermediates. In particular, the bis-type nitrogen-containing heterocyclic compound has been attracting attention as a material exhibiting new functions in addition to the above-mentioned usefulness. However, a compound in which a 5- or 6-membered nitrogen-containing heterocycle is introduced into the peri position of a tricyclic aromatic compound such as xanthene has not been known so far.

[0003]

DISCLOSURE OF THE INVENTION An object of the present invention is to provide a compound having a nitrogen-containing heterocycle linked to the peri position of a tricyclic aromatic compound having a high light absorption rate, a process for producing the same and a synthetic intermediate thereof. Is.

[0004]

SUMMARY OF THE INVENTION The above objects of the present invention are as follows.
First, it was achieved by the following compound and production method. (1) A compound represented by the following general formula (I).

[0005]

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(In the formula, R1, R2, R3, R4, R5 and R6 each represent a hydrogen atom or a substituent. Y1 is an oxygen atom, a sulfur atom or> N (R7), and Y2 is an oxygen atom or a sulfur atom. ,> N (R8) or> C (R9) (R1
0) (wherein R7, R8, R9, and R10 represent a hydrogen atom, an alkyl group, an aryl group, and an oxygen atom, respectively). A1 and A2 each represent a 5- or 6-membered nitrogen-containing heterocycle. (2) A compound represented by the following general formula (II) is represented by the following general formula:
A method for producing a compound represented by the general formula (I) according to item (1), which comprises reacting with a compound represented by (III-a) and a compound represented by (III-b).

[0007]

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(Wherein R1, R2, R3, R4, R5,
R6, Y1, Y2, A1 and A2 have the same meanings as defined in the general formula (I) in the item (1). X represents a leaving group. ) (3) A compound represented by the following general formula (III).

[0009]

[Chemical 6]

Wherein R1, R2, R3, R4, R5,
R6, Y1 and Y2 each have the same meaning as defined in the general formula (I) in the item (1). )

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION The compound represented by formula (I) is described in detail below. R1, R2, R3, R
4, R5 and R6 are each a hydrogen atom, an alkyl group having 1 to 20 carbon atoms [eg, methyl, ethyl, n-propyl, n
-Butyl, t-butyl, n-pentyl, n-hexyl,
An n-heptyl group, an n-octyl group and the like may be further substituted. Examples of the substituent include a halogen atom (eg, chlorine, bromine, iodine, fluorine atom), a nitro group, an alkoxy group (eg, methoxy, ethoxy), an aryloxy group (eg, phenoxy), an amide group, an alkynyl group, an alkenyl group. Group, carbamoyl group,
Examples thereof include a sulfo group, a hydroxy group and a carboxy group. Hereinafter, the substituent group X will be referred to. ], An aryl group having 1 to 20 carbon atoms (eg, phenyl, 1-naphthyl, 2-naphthyl and the like, which may be substituted. Examples of the substituent include the above-mentioned Substituent Group X) and carbon. Number 1-2
An alkoxy group of 0 (eg methoxy, ethoxy, n
-Butoxy, n-propoxy and the like, which may be substituted. Examples of the substituent include the substituent group X described above. ), An aryloxy group having 1 to 20 carbon atoms (for example,
Phenoxy, 1-naphthoxy, 2-naphthoxy and the like, which may be substituted. Examples of the substituent include the substituent group X described above. ), A carboxy group, a sulfo group, a hydroxy group, a cyano group, a halogen atom (eg, fluorine, chlorine, bromine, iodine), an alkoxycarbonyl group having 1 to 20 carbon atoms (eg, methoxycarbonyl, ethoxycarbonyl, phenoxy). Carbonyl, benzylcarbonyl, etc., which may be substituted, and examples of the substituents include the above-mentioned Substituent Group X.), an acyloxy group having 1 to 20 carbon atoms (eg, acetyloxy, propionyloxy, etc.). Examples of the substituent include the above-mentioned Substituent Group X.) and an acyl group having 1 to 20 carbon atoms (for example, acetyl, propionyl, benzoyl, mesyl, etc.), which are substituted. As the substituent, the above-mentioned substituent group X can be used.
Is raised. ), And a carbamoyl group having 1 to 20 carbon atoms (eg, carbamoyl, N, N-dimethylcarbamoyl, morpholinocarbamoyl, etc., which may be substituted. Examples of the substituents include the above-mentioned substituent group X). And an alkylthio group having 1 to 20 carbon atoms (eg, methylthio, ethylthio, etc., which may be substituted. Examples of the substituent include the above-mentioned substituent group X).

R1, R2, R3, R4, R5 and R6 are preferably a hydrogen atom, a halogen atom, an alkyl group or an aryl group. R1, R3, R4 and R6 are particularly preferably hydrogen atoms, and R2 and R5 are particularly preferably t-butyl groups or hydrogen atoms.

Y1 is an oxygen atom, a sulfur atom or> NR
7 Here, R7 is a hydrogen atom, an oxygen atom, an alkyl group or an aryl group, and examples thereof include those mentioned above. Y1 is preferably an oxygen atom. Y2 is an oxygen atom, a sulfur atom,> N-R8 or> C (R9) (R
10). Here, R8, R9 and R10 are each a hydrogen atom, an oxygen atom, an alkyl group or an aryl group, and examples thereof include those mentioned above. Y2 is preferably> N-R8 or> C (R9) (R10).

Each of A1 and A2 is a pyridine ring having 1 to 20 carbon atoms (eg, 2-pyridyl, 3-pyridyl, 4-pyridyl) which may be substituted. The substituent has 1 to 20 carbon atoms. Alkyl group (for example, methyl, ethyl, n-propyl, n-butyl, etc.), C1-20
Aryl groups (eg, phenyl, 1-naphthyl, 2
-Naphthyl, etc.) or the above substituent group X. The substituent is preferably an alkyl group, a halogen atom or an alkylthio group. Examples of the substituted pyridine ring include 2- (3-methyl) pyridyl, 3- (2-methyl) pyridyl, 4- (2-methyl) pyridyl and 2- (4
-Ethyl) pyridyl, 3- (2-butyl) pyridyl, 4
-(3-Propyl) pyridyl, 2- (3-chloro) pyridyl, 3- (2-chloro) pyridyl, 4- (2-chloro) pyridyl, 2- (3-bromo) pyridyl, 3- (4
-Bromo) pyridyl, 2- (5-iodo) pyridyl, 2
Examples include-(3-methylthio) pyridyl, 3- (2-methylthio) pyridyl, 4- (2-ethylthio) pyridyl and the like. ), 1-20 pyridinium rings (eg, 2- (1-hydroxy) pyridinium, 3- (1-
Hydroxy) pyridinium, 4- (1-hydroxy) pyridinium, 2- (1-methyl) pyridinium, 3-
(1-methyl) pyridinium, 4- (1-methyl) pyridinium, 2- (1-phenyl) pyridinium, 3-
(1-phenyl) pyridinium, 4- (1-phenyl)
Pyridinium, which may be substituted. As the substituent, an alkyl group having 1 to 20 carbon atoms (eg, methyl, ethyl, n-propyl, n-butyl, etc.), an aryl group having 1 to 20 carbon atoms (eg, phenyl, 1-naphthyl, 2-naphthyl, etc.) ) Or the above substituent group X. The substituent is preferably an alkyl group, a halogen atom or an alkylthio group. ), A quinoline ring having 1 to 26 carbon atoms (for example, 2-quinoline, 3-quinoline, 4
-Quinoline, 5-quinoline, 6-quinoline, 7-quinoline, 8-quinoline, which may be substituted. As the substituent, an alkyl group having 1 to 20 carbon atoms (eg, methyl, ethyl, n-propyl, n-butyl, etc.), an aryl group having 1 to 20 carbon atoms (eg, phenyl, 1-naphthyl, 2-naphthyl, etc.) ) Or the above substituent group X
Is raised. The substituent is preferably an alkyl group, a halogen atom or an alkylthio group. Examples of the substituted quinoline ring include 2- (3-methyl) quinoline and 4-
(2-methyl) quinoline, 5- (2-methyl) quinoline, 6- (4-methyl) quinoline, 3- (2-ethyl)
Quinoline, 8- (3-propyl) quinoline, 2- (3-
Chloro) quinoline, 2- (3-fluoro) quinoline, 4
-(2-chloro) quinoline, 6- (2-chloro) quinoline, 2- (3-bromo) quinoline, 3- (4-bromo)
Examples include quinoline, 2- (6-iodo) quinoline, 2- (3-methylthio) quinoline, 6- (2-methylthio) quinoline, 4- (2-ethylthio) quinoline, 6- (2-phenylthio) quinoline. . ) Or a quinolinium ring having 1 to 26 carbon atoms (for example, 5- (1-hydroxy) quinolinium, 3- (1-hydroxy) quinolinium, 8- (1-hydroxy) quinolinium, 2-
(1-methyl) quinolinium, 4- (1-methyl) quinolinium, 6- (1-methyl) quinolinium, 2- (1
-Phenyl) quinolinium, 7- (1-phenyl) quinolinium, 4- (1-phenyl) quinolinium,
It may be substituted. 1 to 20 carbon atoms as a substituent
Is an alkyl group (for example, methyl, ethyl, n-propyl, n-butyl, etc.), an aryl group having 1 to 20 carbon atoms (for example, phenyl, 1-naphthyl, 2-naphthyl, etc.) or the above substituent group X is can give. The substituent is preferably an alkyl group, a halogen atom or an alkylthio group. ), A thiazole ring having 1 to 20 carbon atoms (for example,
2-thiazolyl and 4-thiazolyl, which may be substituted. As the substituent, an alkyl group having 1 to 20 carbon atoms (eg, methyl, ethyl, n-propyl, n-butyl, etc.), an aryl group having 1 to 20 carbon atoms (eg, phenyl, 1-naphthyl, 2-naphthyl, etc.) ) Or the above substituent group X. Examples of the substituted thiazole ring include 2- (4-methyl) thiazolyl, 2-
They are (4,5-dimethyl) thiazolyl and 2- (4-phenyl) thiazolyl. A thiazolium ring having 1 to 20 carbon atoms (for example, 2- (3-methyl) thiazolium, 2-
It is (3,4-dimethyl) thiazolium. ), A benzothiazole ring having 1 to 20 carbon atoms (for example, 2-benzothiazolyl, 4-benzothiazolyl, 5-benzothiazolyl, 7-benzothiazolyl, which may be substituted. As a substituent, an alkyl group having 1 to 20 carbon atoms may be used. Group (for example, methyl, ethyl, n-propyl, n-butyl, etc.), aryl group having 1 to 20 carbon atoms (for example, phenyl, 1-naphthyl, 2-naphthyl, etc.) or the above substituent group X. Examples of the substituted benzothiazole ring include 2- (5-chloro) benzothiazolyl, 2- (5,6-dimethyl) benzothiazolyl, 4-
(2-methyl) benzothiazolyl, 5- (2-methyl)
They are benzothiazolyl and 7- (2-methyl) benzothiazolyl. A benzothiazolium ring having 1 to 20 carbon atoms (for example, 2- (3-methyl) benzothiazolium, 4-
It is (2,3-dimethyl) benzothiazolium. ),
An oxazole ring having 1 to 20 carbon atoms (eg, 2-oxazolyl, 4-oxazolyl, which may be substituted. As a substituent, an alkyl group having 1 to 20 carbon atoms (eg, methyl, ethyl, n-propyl). , N-butyl, etc.), an aryl group having 1 to 20 carbon atoms (eg, phenyl, 1-naphthyl, 2-naphthyl, etc.) or the above substituent group X. Examples of the substituted oxazole ring include 2 -(4-methyl) oxazolyl, 2-
They are (4,5-dimethyl) oxazolyl and 2- (4-phenyl) oxazolyl. Oxazolium ring having 1 to 20 carbon atoms (for example, 2- (3-methyl) oxazolium and 2- (3,4-dimethyl) oxazolium), benzoxazole ring having 1 to 20 carbon atoms (for example, 2-benzo). Oxazolyl, 4-benzoxazolyl, 5-benzoxazolyl, 7-benzoxazolyl, which may be substituted, as a substituent, an alkyl group having 1 to 20 carbon atoms (for example, methyl , Ethyl, n
-Propyl, n-butyl, etc.), an aryl group having 1 to 20 carbon atoms (eg, phenyl, 1-naphthyl, 2-naphthyl, etc.) or the above-mentioned substituent group X. Examples of the substituted benzoxazole ring include 2- (5
-Chloro) benzoxazolyl, 2- (5,6-dimethyl) benzoxazolyl, 4- (2-methyl-5-phenyl) benzoxazolyl. A benzoxazolium ring having 1 to 20 carbon atoms (for example, 2- (3-methyl))
They are benzoxazolium and 4- (2,3-dimethyl) benzoxazolium. ), An imidazole ring having 1 to 20 carbon atoms (eg, 2-imidazolyl, 4-imidazolyl, which may be substituted. As a substituent, an alkyl group having 1 to 20 carbon atoms (eg, methyl, ethyl, n -Propyl, n-butyl, etc.), having 1 to 20 carbon atoms
Aryl groups (eg, phenyl, 1-naphthyl, 2
-Naphthyl, etc.) or the above substituent group X. Examples of the substituted imidazole ring include 2-
They are (1,4-dimethyl) imidazolyl and 2- (4,5-dimethyl) imidazolyl. An imidazolium ring having 1 to 20 carbon atoms (for example, 2- (1,3-dimethyl) imidazolium, 2- (1,3-diethyl) imidazolium), a benzimidazole ring having 1 to 20 carbon atoms ( For example, it is 2-benzimidazolyl, which may be substituted.The substituent is an alkyl group having 1 to 20 carbon atoms (for example, methyl, ethyl, n-propyl, n-).
Butyl, etc.), an aryl group having 1 to 20 carbon atoms (eg, phenyl, 1-naphthyl, 2-naphthyl, etc.) or the above substituent group X. Examples of the substituted benzimidazole ring are 2- (1-methyl) benzoxazolyl, 2- (1,6-dimethyl) benzimidazolyl and 4- (1,2-dimethyl) benzimidazolyl. Benzimidazolium ring having 1 to 20 carbon atoms (for example, 2- (1,3-dimethyl) benzimidazolium and 4- (1,2,3-trimethyl) benzimidazolium). As preferable substituents, Examples thereof include a methyl group, an ethyl group, a chlorine atom, a bromine atom, a methylthio group, an ethylthio group and a sulfo group.

Specific examples of the compound represented by formula (I) of the present invention are shown below, but the present invention is not limited thereto.

[0016]

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[0017]

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[0018]

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[0019]

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[0020]

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[0021]

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[0022]

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[0023]

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The compound represented by the general formula (I) is obtained by converting the compound represented by the general formula (II) into the compound represented by the general formula (III-
It can be obtained by reacting the compound represented by a) or (III-b) with a coupling reaction.

[0025]

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(Wherein R1, R2, R3, R4, R5,
R6, Y1, Y2, A1 and A2 are as defined above. X represents a leaving group. ) Specific examples of the compound represented by formula (II) of the present invention are shown below, but the present invention is not limited thereto.

[0027]

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Hereinafter, X and reaction conditions will be described in detail.
X represents a leaving group. A leaving group is Jerry Marc
By h, Advanced Organic Chemi
story-Reactions, mechanism
s, and structure-, Third Ed
edition, p. 179, John Wiley & Son
s company (1985), specifically, ibid., pages 310 to 316, pages 466, 577,
Examples thereof include those described on page 895. For example, a halogen atom (fluorine, chlorine, bromine, iodine atom), carbon number 1
Examples include an alkyl sulfonate having 20 to 20 carbon atoms (eg, methyl sulfonate, trifluoromethane sulfonate, etc.) or an aryl sulfonate having 1 to 20 carbon atoms (eg, paratoluene sulfonate, etc.). A halogen atom and an alkyl sulfonate group are preferable, and a bromine atom, an iodine atom and a trifluoromethane sulfonate group are preferable.

The palladium catalyst may be 0-valent or 2-valent, and include palladium acetate, palladium chloride, tetrakistriphenylphosphine palladium, bistriphenylphosphine palladium dichloride, bisbenzonitrile palladium dichloride, bisdiphenylphosphinoethanopalladium dichloride, bisdiphenyl. Examples thereof include phosphinopropanopalladium dichloride and bisdiphenylphosphinoferrocenopalladium dichloride. A P compound or As compound may be added as a ligand of the palladium catalyst. Examples of the ligand include triphenylphosphine, tritolylphosphine, trifurylphosphine and the like. Preferred palladium catalysts are palladium acetate, tetrakistriphenylphosphine palladium, bistriphenylphosphine palladium dichloride, bisdiphenylphosphinoferrocenopalladium dichloride. In the reaction of the present invention, the compound represented by the general formula (III-a) is usually added in an amount of 1 × 10 ⁻⁴ to 1 mol of the compound of the general formula (II).
The amount used is 1.0 mol, preferably 1 × 10 ^-2 to 1 × 10 ^-1 mol. The amount of the compound represented by the general formula (II-b) used is the same as that of the compound represented by the general formula (II-a).

The reaction solvent may be an organic solvent homogeneous system or an organic solvent-water two-phase system, and preferable organic solvents include dimethylformamide, dimethylacetamide, acetonitrile and toluene. As a preferable two-phase system, toluene and methanol-water are preferable. Particularly preferred reaction solvents are dimethylformamide, toluene and methanol-water.

It is preferable to add a base to the reaction system.
The base may be an inorganic base or an organic base, and preferred bases include sodium carbonate, potassium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, triethylamine, diazabicycloundecene (DBU) and the like. A particularly preferred base is sodium carbonate.

The reaction temperature is preferably 20 ° C. or higher and 180 ° C. or lower, particularly preferably 60 to 140 ° C.

The reaction time is preferably 10 minutes or longer and 30 hours or shorter, particularly preferably 10 minutes to 10 hours.

[0034]

Next, the present invention will be described in more detail with reference to examples.

Example 1 (Synthesis of Compound 58)

[0036]

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2.1 equivalent of n-BuL1 solution was added at −78 ° C. to a THF solution containing 1.0 g of the raw material (C-1) to obtain −78.
After stirring at 30 ° C. for 30 minutes, 0.90 g of boric acid trimethyl ester was added, and the temperature was gradually raised to room temperature. After adding water to the reaction solution, the organic matter was extracted with methylene chloride, dried and the solvent was distilled off in an appropriate amount, and the residue was crystallized from hexane. The obtained crude crystals were purified by crystallization from a methanol / hexane solution to give 0.4 g of the target compound (58).
Obtained. White crystal Melting point: 300 ° C or higher IR (KBr) 3350, 2955, 2860, 160
2,1430,1380,1270,1218,113
8, 1100, 1020, 890, 840, 780, 7
^{62cm -1 1 H-NMR (CDCl} 3) δ1.31 (s, 18
H), 1.60 (s, 6H), 7.54 (s, 2H),
7.62 (s, 2H), 8.33 (s, 4H)

Example 2 (Synthesis of Compound 2)

[0039]

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120 mg of compound (C-2) and 0.1 g of tetrakistriphenylphosphine palladium (14 m
mol%), 5 ml of 2N aqueous sodium carbonate solution and 10 ml of toluene were added at room temperature to give compound (58) 100 m.
Then, g of a methanol solution was added, followed by stirring at 80 ° C. for 3 hours. After cooling the reaction solution, the organic matter was extracted with methylene chloride, dried and the solvent was distilled off under reduced pressure. The residue was purified by alumina chromatography (eluent = methylene chloride: methanol) to obtain 75 mg of the target compound (2). Obtained. White crystal Melting point 275 ° C IR (KBr) 3440, 1650, 1570, 142
^{0,1242,998,824,804cm -1 1 H-NMR (CDCl} 3) δ1.36 (s, 18
H), 1.74 (s, 6H), 7.15 to 7.20.
(M, 6H), 7.51 (d, 2H, J = 2Hz),
8.38 (dd, 4H, J = 5 Hz, J = 2 Hz) Elemental analysis Actual value C82.96, H7.72, N5.90 (%) Calculated value C83.15, H7.61 and N5.88 (%)

Example 3 (Synthesis of Compound 11)

[0042]

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140 mg of compound (C-3) and 0.1 g of tetrakistriphenylphosphine palladium (14 m
5% of 2N sodium carbonate and 10 ml of toluene were added to (mol%) at room temperature, and a methanol solution of 100 mg of the compound (56) was added next, followed by stirring at 80 ° C. for 6 hours. After cooling the reaction solution, extract organic matter with methylene chloride,
After drying, the solvent was distilled off under reduced pressure. The residue was purified by alumina chromatography (eluent = methylene chloride: methanol) to obtain 72 mg of the target compound (11). White crystal Melting point 254 ° C IR (KBr) 2960,1603,1550,148
0,1452,1398,1370,1280,125
^{9,1098,882,840cm -1 1 H-NMR (CDCl} 3) δ1.36 (s, 18
H), 1.74 (s, 6H), 2.38 (s, 6H),
7.1-7.2 (m, 4H), 7.18 (d, 2H, J
= 2.3 Hz), 7.52 (d, 2H, J = 2.3H
z), 8.38 (d, 2H, J = 5.1Hz)

Example 4 (Synthesis of Compound 18)

[0045]

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110 mg of compound (C-4) and 0.1 g of tetrakistriphenylphosphine palladium (18 m
mol%), 5 ml of 2N aqueous sodium carbonate solution and 10 ml of toluene were added at room temperature to give compound (58) 100 m.
Then, g of a methanol solution was added, and the mixture was stirred at 80 ° C. for 1 hour. After cooling the reaction solution, the organic matter was extracted with methylene chloride, dried and the solvent was distilled off under reduced pressure. The residue was purified by alumina chromatography (eluent = methylene chloride: methanol) to obtain 31 mg of the target compound (18). White crystal Melting point 237 ° C IR (KBr) 2960, 1740, 1616, 160
2,1571, 1500, 1442, 1361, 128
1,1250,1120,880,839,762cm
^{-1 11} H-NMR (CDCl ₃ ) δ 1.35 (s, 18
H), 1.81 (s, 6H), 2.44 (s, 6H),
6.78 (t, 2H, J = 7.7 Hz), 6.94
(D, 2H, J = 8.4 Hz), 7.18 (dd, 2
H, J = 6 Hz, J = 1 Hz), 7.32 (d, 2H,
J = 2.3 Hz), 7.38 (dd, 2H, J = 6H
z, J = 2 Hz), 7.45 (d, 2H, J = 2.3H)
z), 7.79 (d, 2H, J = 8.4 Hz)

Example 5 (Synthesis of Compound 25)

[0048]

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47 mg of compound (11) and 150 m of MeI
A solution of g in 5 ml of acetonitrile was heated and stirred at 80 ° C. for 30 minutes, the reaction solution was cooled, 5 ml of hexane was added, and the precipitated crystals were filtered off to obtain 43 mg of the target compound (25). White crystal Melting point: 300 ° C or higher IR (KBr) 3450, 2960, 1640, 156
1,1442,1401,1368,1280,126
0,1222,1160,1039,850,630c
^{m -1 1 H-NMR (DMSO} -d 6) δ1.36 (s, 18
H), 1.79 (s, 6H), 2.70 (s, 6H),
4.24 (s, 6H), 7.39 (s, 2H), 7.8
0 (s, 2H), 7.92 (d, 2H, J = 6.6H
z), 8.19 (s, 2H), 8.70 (d, 2H, J
= 6.6Hz)

Test Example 1 40 g of 50 g gelatin aqueous solution having a gelatin concentration of 70 g / L
At 0 ° C., the compound (2) of the present invention or the comparative compound of 0.
5 ml of a solution prepared by adding a 0005 mol / L methanol solution is circularly coated on a polyethylene terephthalate substrate to make the gelatin concentration on the substrate 30 mg / m ² . This was dried at 25 ° C. and 60 RH for 12 hours to obtain a gelatin dry film (1 and 2). The UV-visible absorption spectrum of this gelatin dry film was measured by Hitachi UV-3100. The absorption intensity in the wavelength component longer than 250 nm was integrated with respect to the horizontal axis (eV), and the integration ratio S (S = value of gelatin film 1 / value of gelatin film 2) was obtained.
It became 1.22.

[0051]

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From the above results, it can be seen that the compound of the present invention has a higher absorption of the coating film than the comparative compound, and has a higher light absorptivity.

[0053]

According to the present invention, a nitrogen-containing heterocyclic compound having a high light absorptivity can be provided.

Front page continuation (51) Int.Cl. ⁶ Identification code Office reference number FI Technical display location C07D 401/14 213 C07D 401/14 213 409/04 215 409/04 215 409/14 213 409/14 213 411 / 14 411/14 413/14 311 413/14 311 417/14 213 417/14 213 311 311 C09B 11/28 C09B 11/28 M C09K 3/00 104 C09K 3/00 104B

Claims (3)

[Claims] 1. A compound represented by the following general formula (I). Embedded image (In the formula, R1, R2, R3, R4, R5 and R6 each represent a hydrogen atom or a substituent. Y1 is an oxygen atom, a sulfur atom or> N (R7), Y2 is an oxygen atom, a sulfur atom,
> N (R8) or> C (R9) (R10) (where
R7, R8, R9 and R10 each represent a hydrogen atom, an alkyl group, an aryl group or an oxygen atom. ). A1 and A2 each represent a 5- or 6-membered nitrogen-containing heterocycle. ) 2. A compound represented by the following general formula (II) and a compound represented by the following general formula (III-a) and (III-b):
The method for producing the compound represented by the general formula (I) according to claim 1, wherein the compound represented by the formula (1) is reacted. Embedded image (In the formula, R1, R2, R3, R4, R5, R6, Y1,
Y2, A1 and A2 have the same meanings as defined in the general formula (I) of claim 1, respectively. X represents a leaving group. ) 3. A compound represented by the following general formula (III). Embedded image (In the formula, R1, R2, R3, R4, R5, R6, Y1 and Y2 have the same meanings as defined in the general formula (I) of claim 1.)