JP2802698B2 - Method for producing 1-N-alkyl- [1,2,4] triazoles and 1H-pyrrolo- [1,2-b] [1,2,4] triazoles - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to 1H-pyrrolo- [1,
2-b] [1,2,4] triazoles and a process for producing 1-N-alkyl- [1,2,4] triazoles useful as synthetic intermediates thereof.

[0002]

2. Description of the Related Art 1-N-alkyl- [1,2,4] triazole derivatives are useful as synthetic intermediates for dyes, medicines and agricultural chemicals. On the other hand, 1H-pyrrolo- [1,2-b]
[1,2,4] triazoles are useful as intermediates in the synthesis of biologically active substances in dyes, photographic couplers, pharmaceuticals or agricultural chemicals. For example, an example of a photographic coupler can be found in JP-A-62-279340.

By the way, 1H-pyrrolo- [1,2-b]
The following literatures are known as a method for synthesizing [1,2,4] triazoles. That is, Ukr. Khim. Zh., 38, 1142 (197
2). Ukr. Khim. Zh., 41, 181 (197
5). Ukr. Khim. Zh., 41, 252 (197
5). Ukr. Khim. Zh., 41, 1053 (197
5). Synthesis, 414 (1973). Etc.

However, these 1H-pyrrolo-
In the method for synthesizing [1,2-b] [1,2,4] triazoles, it was difficult to synthesize a compound having an electron-withdrawing group at the 6-position and the 7-position at the same time. Therefore, 1H-pyrrolo- [1,
2-b] Development of a synthesis method capable of obtaining a compound having a strong electron-withdrawing group at each of the 6-position and the 7-position of [1,2,4] triazole in good yield is strongly desired.

[0005]

Accordingly, an object of the present invention is to provide a 1-N-alkyl-alkyl compound useful as a synthetic intermediate.
To provide an efficient method for synthesizing [1,2,4] triazoles, and to provide 1H-pyrrolo- [1,2-b] [1,2,1] having electron-withdrawing groups at the 6-position and the 7-position, respectively.
4] To provide a method for synthesizing triazoles with good yield.

[0006]

Means for Solving the Problems The present inventor has made studies to overcome such conventional problems, and as a result, has accomplished the present invention described below. (1) The triazole represented by the general formula [I] is alkylated using an N-alkylating agent substituted with Y and Z,

[0007]

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A method for producing 1-N-alkyl- [1,2,4] triazoles represented by the general formula [II]. General formula (II)

[0009]

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(In the general formulas (I) and (II), X and Y each represent a cyano group or -COR ', Z represents a halogen atom, and Ar represents an unsubstituted or substituted benzene aryl. A heterocyclic group or a heterocyclic group;
Is a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylamino group,
Represents an arylamino group, a heterocyclic amino group or an unsubstituted amino group, and R 'is an alkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylamino group, an arylamino group, a heterocyclic amino group or an unsubstituted amino group. Represents (2) A compound represented by the general formula [III] obtained by halogenating a 1-N-alkyl- [1,2,4] triazole represented by the general formula [II] produced by the method (1). With the general formula [III]

[0011]

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Thereafter, a ring-closing reaction is carried out to obtain 1H-pyrrolo- [1,2-b] [1,2,
4) A method for producing triazoles. General formula (IV)

[0013]

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(In the general formulas [III] and [IV], X, Y,
Z and Ar have the same meanings as X, Y, Z and Ar in formula (II), respectively, and W represents a halogen atom. )

Next, general formulas [I], [II], [II]
The compounds represented by I] and [IV] will be described in detail. In the general formulas (I), (II), (III) or (IV), X is preferably a cyano group or -CO
R has the following R. That is, R is preferably a hydrogen atom, a linear or branched alkyl group having 1 to 36 (more preferably 1 to 24) carbon atoms (more preferably 1 to 24), and a C number of 2 to 36 ( More preferably 2
To 24) linear or branched alkenyl group, C 3 to 36 (more preferably (3 to 24) 3 to 12 membered cycloalkyl group, C 6 to 36 (more preferably 6 to 36)
24) aryl group having 1 to 34 C atoms (more preferably 1
To 24), an alkoxy group having 1 to 36 (more preferably 1 to 24) C atoms, an aryloxy group having 6 to 36 (more preferably 6 to 24) C atoms, a C 1 to 36 (more preferably) Preferably an alkylamino group having 1 to 24) and a C number of 6 to
36 (more preferably 6 to 24) arylamino groups,
Represents a heterocyclic oxy group having 1 to 36 (more preferably 1 to 24) carbon atoms, an amino group having 1 to 36 (more preferably 1 to 24) carbon atoms, or an unsubstituted amino group; A group other than the substituted amino group may be a substituent (eg, a halogen atom, a hydroxyl group, a carboxyl group, a sulfo group,
Cyano group, nitro group, amino group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aryl group,
An alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, an acyl group, an acyloxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbonamide group, a sulfonamide group, a carbamoyl group, a sulfamoyl group, A ureido group, an alkoxycarbonylamino group, a sulfamoylamino group, an alkoxysulfonyl group, an imide group or a heterocyclic group, which is referred to as a substituent group A). X is preferably a cyano group and -C
OR having the following R: That is, R is preferably an unsubstituted amino group, linear or branched or unsubstituted or substituted group (alkoxy group, alkylthio group, aryloxy group, arylthio group, alkylsulfonyl group, arylsulfonyl group, aryl group, An alkyl group having an alkoxycarbonyl group, an epoxy group, a cyano group or a halogen atom (for example, n-octyl,
n-decyl, n-dodecyl, n-hexadecyl, 2-ethylhexyl, 3,5,5-trimethylhexyl, 2-
Ethyl-4-methylpentyl, 2-hexyldecyl, 2
-Heptylundecyl, 2-octyldodecyl, 2,
4,6-trimethylheptyl, 2,4,6,8-tetramethylnonyl, benzyl, 2-phenethyl, 3- (t-
Octylphenoxy) propyl, 3- (2,4-di-t)
-Pentylphenoxy) propyl, 2- (4-biphenylyloxy) ethyl, 3-dodecyloxypropyl, 2
-Dodecylthioethyl, 9,10-epoxyoctadecyl, dodecyloxycarbonylmethyl, 2- (2-naphthyloxy) ethyl), unsubstituted or substituted (for example, halogen atom, aryl group, alkoxy group, alkylthio group, aryloxy group) Alkenyl group having an arylthio group or an alkoxycarbonyl group (e.g., allyl, 10-undecenyl, oleyl, citronellyl, cinnamyl), unsubstituted or substituted (halogen atom, alkyl group, cycloalkyl group, aryl group, alkoxy group or aryl) A cycloalkyl group (e.g., cyclopentyl, cyclohexyl, 3,5-dimethylcyclohexyl, 4-t-butylcyclohexyl) having an unsubstituted or substituted group (substituent group A);
A condensed aryl group (eg, phenyl, 2-t
-Butylphenyl, 2-naphthyl), unsubstituted or substituted (halogen atom, cyano group, alkyl group, aryl group, alkoxy group, aryloxy group, arylthio group, alkylsulfonyl group, arylsulfonyl group, carbonamide group, sulfone A heterocyclic group having an amide group (e.g., 2-pyridyl, 2-thienyl), an unsubstituted or substituted group (an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, an alkylsulfonyl group,
An alkoxy group having an arylsulfonyl group, an aryl group, an alkoxycarbonyl group, an epoxy group, a cyano group or a halogen atom (for example, methoxy, ethoxy, isopropoxy, isobutoxy, n-octyloxy, n-
Decyloxy, n-dodecyloxy, n-hexadecyloxy, 2-ethylhexyloxy, 3,5,5-trimethylhexyloxy, 2-ethyl-4-methylpentyloxy, 2-hexyldecyloxy, 2-heptylundecyloxy , 2-octyldodecyloxy, 2,
4,6-trimethylheptyloxy, 2,4,6,8-
Tetramethylnonyloxy, benzyloxy, 2-phenethyloxy, 3- (t-octylphenoxy) propoxy, 3- (2,4-di-t-pentylphenoxy) propoxy, 2- (4-biphenylyloxy) ethoxy,
3-dodecyloxypropoxy, 2-dodecylthioethoxy, 9,10-epoxyoctadecyloxy, dodecyloxycarbonylmethoxy, 2- (2-naphthyloxy) ethoxy, 7,7-dimethyl-2- (3 ', 3'-
Dimethylbutyl) -5-methyloctyloxy), unsubstituted or substituted aryloxy group (substituent group A) (eg, phenoxy, 2-t-amylphenoxy, 4-dodecyloxyphenoxy), unsubstituted or substituted Alkylamino group having a group (alkoxy group, alkylthio group, aryloxy group, arylthio group, alkylsulfonyl group, arylsulfonyl group, aryl group, alkoxycarbonyl group, epoxy group, cyano group or halogen atom) (for example, ethylamino, n-dodecylamino), an unsubstituted or substituted (substituent group A) or an optionally substituted arylamino group (eg, anilino group, 2-chloroanilino group, 2-naphthylamino group), unsubstituted or Substituents (halogen atom, cyano group, alkyl group, Aryl group, an alkoxy group, an aryloxy group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a carbonamido group, a heterocyclic oxy group having a sulfonamide group) (e.g., 1-
Phenyltetrazol-5-oxy, 2-tetrahydropyranyloxy), unsubstituted or substituted (halogen atom, cyano group, alkyl group, aryl group, alkoxy group, aryloxy group, arylthio group, alkylsulfonyl group, arylsulfonyl group) , Carbonamido group,
A heterocyclic amino group having a sulfonamide group (eg, pyridyl-2-amino).

X is particularly preferably a cyano group and -C
OR having the following R: That is, R is the aforementioned linear or branched substituted alkoxy group and an unsubstituted or substituted aryloxy group.

[0017]

In the general formula [III], W is preferably a fluorine atom, a chlorine atom, a bromine atom or an iodine atom;
Particularly preferred are a chlorine atom and a bromine atom.

In the general formulas [II] and [III],
Z is preferably a chlorine atom or a bromine atom.

In the general formulas [I], [II], [III] and [IV], Ar is preferably an aryl group having 6 to 36 C (more preferably 6 to 30) or a C having 1 to 36 C.
(More preferably 1 to 30) heterocyclic group (preferably a 4- to 8-membered ring as a hetero ring and a nitrogen atom, a sulfur atom and an oxygen atom as a hetero atom).

Ar is preferably an unsubstituted or unsubstituted benzene-based aryl group (for example, phenyl, 3-nitrophenyl, 4-nitrophenyl, 4-cyanophenyl, 3,4-dicyano). Phenyl,
3,4-dimethoxycarbonylphenyl, 3- (2-octyloxy-5-t-octyl) phenylsulfonylaminophenyl, 3,5-dichlorophenyl, 4- {1
-(2,4-di-t-amylphenoxy) propanoylaminodiphenyl, 3- (2,4-di-t-amylphenoxyacetylamino) phenyl), and unsubstituted or substituted groups (halogen atom, cyano group And a heterocyclic group having an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a carbonamide group, and a sulfonamide group (eg, 2-pyridyl, 2-thienyl). . Ar is particularly preferably the aforementioned aryl group.

The triazole represented by the general formula [I] can be synthesized by a known method. For example, JCS, 518 (1961)., JCS, 5149 (1962)., Ange
w.Chem., 72.956 (1960)., Berichte., 97.3436 (196
4). Can be synthesized by the methods described in, etc., the references cited therein, or similar methods.

Next, the derivation from the general formula [I] to [II] (hereinafter referred to as Step 1) will be described in detail. Examples of the N-alkylating agent used in the alkylation in Step 1 include α-chloroacrylonitrile, 1-cyano-1,2
-Dibromoethane, ethyl 2,3-dibromopropionate, methyl 2,3-dibromopropionate, 2,3-dibromoacrylamide and the like.

The base used in Step 1 includes:
Inorganic bases, organic bases, organometallic bases and the like can be used. For example, sodium hydride, 1,8-diazabicyclo [5,4,0] -7-undecene (DBU), 1,5
-Diazabicyclo [4,3,0] -5-nonene (DB
N), triethylamine, 1,1,3,3-tetramethylguanidine, potassium carbonate, sodium carbonate, sodium ethoxide, trimethylbenzylammonium hydroxide, potassium hydride, potassium t-butoxide, sodium acetate, sodium methoxide, potassium Methoxide,
And the like. Among them, organic bases are preferable, and particularly preferable among these organic bases are organic amine bases. For example, DBU, DBN, 1,1,3,3
-Tetramethylguanidine, triethylamine, trimethylbenzylammonium hydroxide, and the like.

The molar ratio of the N-alkylating agent to the compound represented by the formula (I) in Step 1 is 0.01 to 1
000, preferably 0.05 to 20, more preferably 0.5 to 5.0.

The molar ratio of the base to the compound of the formula [I] in Step 1 is from 0.001 to 100, preferably from 0.01 to 50, more preferably from 0.1 to 50.
05 to 0.5.

The solvent used in Step 1 includes methylene base, chloroform, 1,2-dichloroethane, acetonitrile, N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, N-methylpyrrolidone, tetrahydrofuran, dioxane, dimethoxy Ethane, diglyme, benzene, toluene, ethyl acetate, acetone, xylene and the like are used, and in particular, methylene chloride, 1,2-dichloroethane, N, N-dimethylformamide, N, N-dimethylacetamide, tetrahydrofuran, dioxane, toluene Are preferred.

The reaction temperature is -78 ° C to 250 ° C, preferably -10 ° C to 100 ° C, more preferably -5 ° C to 70 ° C.
° C, particularly preferably 5 ° C to 40 ° C. The reaction time is 30 seconds to 72 hours, preferably 10 minutes to 48 hours,
More preferably, it is 20 minutes to 24 hours.

Next, the derivation from the general formula (II) to the formula (III) (hereinafter referred to as Step 2) will be described in detail: Examples of the halogenating agent used in the halogenation in Step 2 include chlorine, sulfuryl chloride, Copper (II) chloride, N-chlorosuccinimide, N-bromocaprolactam, N-bromophthalimide, 1,3-dibromo-5,5-dimethylhydantoin, bromine, N-bromosuccinimide, copper halide (II ) Dioxane dibromide, phenyltrimethylammonium tribromide, pyridinium bromide perbromide, pyrrolidone hydrotribromide, etc., especially sulfuryl chloride, N-chlorosuccinimide, bromine, N-bromosuccinimide, pyridinium bromide perbromide Are preferred.

The molar ratio of the halogenating agent to the compound represented by the general formula [II] in Step 2 is from 0.01 to
100, preferably 0.5 to 10, more preferably 1.0 to 3.0.

As the solvent in Step 2, methylene chloride, chloroform, 1,2-dichloroethane, acetonitrile, N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, dioxane, tetrahydrofuran, water, carbon tetrachloride, Examples include acetic acid, methanol, ethanol, benzene, pyridine, etc., particularly methylene chloride, chloroform, N, N-dimethylformamide, N, N-dimethylacetamide, dioxane, tetrahydrofuran, water, carbon tetrachloride, acetic acid, methanol, ethanol , Benzene, pyridine and the like are preferred.

The reaction temperature is -78 ° C to 150 ° C, preferably -20 ° C to 80 ° C, more preferably -10 ° C to 70 ° C.
° C, particularly preferably -10 ° C to 30 ° C. The reaction time is 1 minute to 72 hours, preferably 15 minutes to 48 hours, more preferably 30 minutes to 36 hours.

Next, the derivation from the general formulas [III] to [IV] (referred to as Step 3) will be described in detail. St
In eo3, the general formula [III] is closed, and [I
V], it is desirable to use a base. In the present invention, the compound represented by the general formula [III] is subjected to a ring-closing reaction and an oxidation reaction in one step to obtain a compound represented by the general formula [I
V] is obtained.

Examples of the base used in Step 3 include sodium carbonate, potassium carbonate, lithium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium hydride, potassium hydride, lithium hydride, potassium t-butoxy, 1,1 and , 3,3-tetramethylguanidine, DBU, DBN, sodium acetate, triethylamine, trimethylsilyloxypotassium, sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, sodium hydroxide, potassium hydroxide, sodium amide, n -Butyllithium, n-methyllithium, t-butyllithium, i-propyllithium and the like, and particularly, sodium hydride, potassium t-butoxy, 1,1,3,3-tetramethylguanidine, DBU, DB , Triethylamine, sodium methoxide, sodium ethoxide, potassium methoxide, n- butyllithium, etc. are preferable.

The general formula of the base in Step 3 [II
The compound (I) has a molar ratio of 0.01 to 10
, Preferably 0.5 to 5.0, more preferably 1.0 to 4.0, and particularly preferably 2.8 to 4.0.
It is.

The solvent in Step 3 includes methylene chloride, chloroform, 1,2-dichloroethane, acetonitrile, N, N-dimethylformamide, N, N-dimethylacetamide, dimethylsulfoxide, N-methylpyrrolidone, tetrahydrofuran, dioxane, dimethoxy Ethane, diclime, benzene, toluene, methanol, ethanol, isopropanol, ethyl acetate, acetone, xylene, petroleum ether, diethyl ether, and the like, and particularly, methylene chloride, chloroform,
Preferred are 1,2-dichloroethane, tetrahydrofuran, dioxane, diethyl ether and the like.

The reaction temperature varies depending on the system used, but is -100.
C. to 100 C., preferably -100 C. to 90 C., more preferably -78 C. to 60 C., particularly preferably -C.
50 ° C to 30 ° C. The addition of the base in Step 3
It is preferable to carry out the reaction slowly so that the reaction temperature in the system does not rise. In particular, it is preferable to carry out in a range of ± 2 ° C.
The reaction time is 30 seconds to 72 hours, preferably 5 minutes to 48 hours.
Time, more preferably 10 minutes to 12 hours.

The product in each Step can be separated from the reaction solution by a conventional method, but may be used as a starting material for the subsequent reaction without any isolation, if necessary. As an appropriate isolation procedure, a recrystallization method, a solvent extraction method, a filtration method, column chromatography, thin-layer chromatography, or the like is used alone or in an appropriate combination.

(Specific examples of compounds) Specific examples of the compounds to which the method of the present invention is applied are shown below, but the invention is not limited thereto. Specific examples of the compound represented by the general formula [I] are shown. In the following structural formula, (t) C ₅ H ₁₁ is -C (CH ₃ ) ₂ C ₂ H
₅ and (t) C ₈ H ₁₇ represent —C (CH ₃ ) ₂ CH ₂ C (CH ₃ ) ₃ .

[0040]

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[0041]

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[0042]

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[0043]

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[0044]

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[0045]

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[0046]

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[0047]

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[0048]

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[0049]

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[0050]

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[0051]

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Next, specific examples of the compound represented by the general formula [II] are shown.

[0053]

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[0054]

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[0055]

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[0056]

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[0057]

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[0058]

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[0059]

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[0060]

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[0061]

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[0062]

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[0063]

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[0064]

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Next, specific examples of the compound represented by the general formula [III] will be shown.

[0066]

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[0067]

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[0068]

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[0069]

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[0070]

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[0071]

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[0072]

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[0073]

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[0074]

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[0075]

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[0076]

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[0077]

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Next, specific examples of the compound represented by the general formula [IV] will be shown.

[0079]

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[0080]

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[0081]

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[0082]

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[0083]

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[0084]

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[0085]

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[0086]

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[0087]

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[0088]

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[0089]

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[0090]

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The compound represented by the general formula [IV] also means each compound in the following equilibrium state.

[0092]

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[0093]

According to the present invention, 1-N-alkyltriazole can be efficiently synthesized. Also, 1-
From N-alkyltriazoles, the desired 1H-pyrrolo [1,2-b] [1,2,4] triazoles having electron-withdrawing groups at the 6-position and the 7-position are synthesized in two steps and in good yield. be able to.

[0094]

Next, the present invention will be described in more detail based on synthesis examples. (Synthesis Example 1) Synthesis of Exemplified Compound (IV-13) Exemplified compound (IV-13) was synthesized by the following route.

[0095]

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30.0 g of (I-13) and 11.4 g of (a) were dissolved in 300 ml of tetrahydrofuran, and 6.0 ml of tetramethylguanidine was added. After stirring at room temperature for 5 hours, 500 ml of ethyl acetate was added, and the ethyl acetate layer washed with water was dried and evaporated, and crystallized with methanol to obtain 27.5 g of (II-13) (yield: 72%). The melting point of (II-13) was 98 ° C. to 99 ° C., and an infrared absorption spectrum of the compound (II-13) confirmed an absorption indicating the presence of a cyano group at 2210 cm ⁻¹ . 27.4 g of the obtained (II-13) was added to tetrahydrofuran 27.
The solution was dissolved in 0 ml, and 27.2 g of pyridinium bromide perbromide was added under cooling with water. After stirring for 5 hours, 500 ml of ethyl acetate was added, and the mixture was washed with water until neutral.
After the ethyl acetate layer was dried and evaporated, the residue was purified by column chromatography to give (III-13)
Was obtained 28.0 g (yield 85%). The obtained (III-
13) 28.0 g was dissolved in 170 ml of tetrahydrofuran, the reaction temperature was kept at -10 ° C, and 9.6 g of 60% sodium hydride was added little by little. After the reaction, ethyl acetate was added and washed with water. The ethyl acetate layer was dried, distilled off, and purified by column chromatography (IV-1).
3.0 g (14% yield) of 3) was obtained.

(Synthesis Example 2) Synthesis of Exemplified Compound (IV-27) Exemplified compound (IV-27) was synthesized by the following route.

[0098]

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Compound (I-27) (50.0 g, 109
mmol) and 2-chloroacrylonitrile (a) (1
2.4 g, 142 mmol) in tetrahydrofuran 50
The solution was dissolved in 0 ml, and 6.6 ml of tetramethylguanidine was added. After stirring at room temperature for 5 hours, ethyl acetate 600m
1 and washed with water. The ethyl acetate layer was dried and distilled off, and crystallized from methanol to give (II-27) as 37.
5 g (63%) were obtained. According to the infrared absorption spectrum measurement of (II-27), an absorption indicating the presence of a cyano group was found to be 221.
It was confirmed at 0 cm ^-1 . The obtained (II-27) (3
7.5 g) 68.9 mmol) in tetrahydrofuran 3
After dissolving in 70 ml, pyridinium bromide perbromide (26.3 g, 82.4 mmol) was added under cooling with water. After stirring for 5 hours, 500 ml of ethyl acetate was added, and the mixture was washed with water until neutral. After the ethyl acetate layer was dried and distilled off, the residue was purified by column chromatography to obtain 33.9 g (79%) of (III-27). The obtained (III-27) (33.9 g, 54.4 mmol)
l) was dissolved in 200 ml of tetrahydrofuran, the reaction temperature was maintained at -10 ° C, and 60% sodium hydride (8.7) was added.
g, 217 mmol) were added in portions. After the reaction, ethyl acetate was added and washed with water. The ethyl acetate layer was dried, distilled off, and purified by column chromatography to obtain 4.4 g (yield 16%) of (IV-27). Other compounds can be synthesized in the same manner.

──────────────────────────────────────────────────続 き Continuation of front page (56) References JP-A-62-289837 (JP, A) (58) Fields investigated (Int. Cl. ⁶ , DB name) C07D 249/08 C07D 401/04 C07D 403 / 12 C07D 487/04 CA (STN) REGISTRY (STN)

Claims (2)

(57) [Claims] 1. An alkylation of a triazole represented by the general formula [I] using an N-alkylating agent substituted with Y and Z, to give a 1-N-alkyl- [ [1,2,4] A method for producing triazoles.
General formula [I] General formula [II] (In the general formulas [I] and [II], X represents a cyano group or -C
OR represents Y, and represents a cyano group or -COR ',
Z represents a halogen atom, Ar represents an unsubstituted or substituted benzene aryl group or a heterocyclic group, and R represents a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, a heterocyclic group, an alkoxy group. Group,
Represents an aryloxy group, a heterocyclic oxy group, an alkylamino group, an arylamino group, a heterocyclic amino group or an unsubstituted amino group, and R ′ is an alkoxy group, an aryloxy group, a heterocyclic oxy group, an alkylamino group, an aryl Represents an amino group, a heterocyclic amino group or an unsubstituted amino group. ) 2. A 1-N-alkyl- [1,2,2] represented by the general formula [II] produced by the method according to claim 1.
4] Halogenating a triazole, a compound of the general formula [III]
The compound represented by formula (IV) is then subjected to a ring closure reaction to give 1H-pyrrolo- [1,2-
b] A method for producing [1,2,4] triazoles. General formula [III] General formula [IV] (In the general formulas [III] and [IV], X, Y, Z and Ar have the same meanings as X, Y, Z and Ar in the general formula (II), respectively, and W represents a halogen atom.)