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WO2012060232A1 - 5-trifluorométhyl-4-nitro-2-isoxazolines et leur procédé de synthèse - Google Patents

5-trifluorométhyl-4-nitro-2-isoxazolines et leur procédé de synthèse Download PDF

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Publication number
WO2012060232A1
WO2012060232A1 PCT/JP2011/074346 JP2011074346W WO2012060232A1 WO 2012060232 A1 WO2012060232 A1 WO 2012060232A1 JP 2011074346 W JP2011074346 W JP 2011074346W WO 2012060232 A1 WO2012060232 A1 WO 2012060232A1
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Prior art keywords
trifluoromethyl
nitro
group
cdcl
nmr
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PCT/JP2011/074346
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English (en)
Japanese (ja)
Inventor
哲男 柴田
洋幸 河合
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Priority to CN2011800512540A priority Critical patent/CN103180303A/zh
Publication of WO2012060232A1 publication Critical patent/WO2012060232A1/fr
Priority to IL225915A priority patent/IL225915A0/en
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the present invention relates to a 5-trifluoromethyl-4-nitro-2-isoxazoline compound and a method for producing the compound.
  • 5-trifluoromethyl-2-isoxazoline compounds have attracted attention as pest control agents.
  • the 5-trifluoromethyl-2-isoxazoline compound is also a useful compound as an intermediate for the production of functional materials such as pharmaceuticals and electronic materials. Due to its usefulness, a great number of 5-trifluoromethyl-2-isoxazoline compounds have been synthesized conventionally. However, all the synthesis methods are building block methods synthesized using a compound having a trifluoromethyl group in advance, and there is no report of a synthesis method in which a trifluoromethyl group is directly introduced into a 2-isoxazoline compound. .
  • Patent Documents 1, 2, and 3 cyclization reaction between hydroxamic acid halides and trifluoromethyl-substituted olefin
  • Patent Documents 4, 5, 6 and Non-Patent Document 1 Reaction with hydroxylamine
  • Patent Documents 4, 5, 6 and Non-Patent Document 1 Reaction with hydroxylamine
  • Patent Documents 4, 5, 6 and Non-Patent Document 1 development of a method for synthesizing a 5-trifluoromethyl-2-isoxazoline compound by directly introducing a trifluoromethyl group into the 2-isoxazoline compound is desired.
  • 5-trifluoromethyl-4-nitro-2-isoxazoline compounds in which a nitro group is introduced at the 4-position of the 5-trifluoromethyl-2-isoxazoline compound have not been reported so far. It is expected to be used as a new basic skeleton for the development of pesticides and as an intermediate for the production of functional materials such as pharmaceuticals and electronic materials.
  • the present invention has been made in view of the above problems, and introduces a trifluoromethyl group directly into a 2-isoxazoline compound, that is, 5-trifluoromethyl-4 by a direct trifluoromethylation method.
  • the main object is to provide a method for producing a -nitro-2-isoxazoline compound and a novel compound group, 5-trifluoromethyl-4-nitro-2-isoxazoline compound.
  • the inventors used (trifluoromethyl) trimethylsilane (CF 3 SiMe 3 ), which is known as a Ruppert reagent, as a trifluoromethylation reagent, and used an electron asking as a reaction substrate.
  • the inventors have also found that only one diastereomer can be obtained by subjecting the obtained 5-trifluoromethyl-4-nitro-2-isoxazoline compound to an acid treatment.
  • the 5-trifluoromethyl-4-nitro-2-isoxazoline compound according to the present invention has the following general formula (1)
  • R 1 and R 2 each independently represent a substituted or unsubstituted alkyl group, alkenyl group, alkynyl group, or aryl group. It is represented by
  • a method for producing a 5-trifluoromethyl-4-nitro-2-isoxazoline compound according to the present invention includes a 5-trifluoromethyl- represented by the general formula (1).
  • a process for producing a 4-nitro-2-isoxazoline compound comprising the following general formula (2)
  • R 1 and R 2 are the same as those in the general formula (1).
  • a (trifluoromethyl) trimethylsilane (CF 3 SiMe 3 ) is reacted with a 4-nitro-2-isoxazole compound represented by the formula:
  • a trifluoromethyl anion is conjugated and added to the 5-position of a 4-nitro-2-isoxazole compound having a nitro group as an electron-attracting group at the 4-position. That is, since the trifluoromethyl group is directly introduced into the 5-position of the 4-nitro-2-isoxazole compound, the 5-trifluoromethyl-4-nitro-2-isoxazoline compound is obtained by the direct trifluoromethylation method.
  • the manufacturing method of can be provided.
  • a 5-trifluoromethyl-4-nitro-2-isoxazoline compound which is a novel compound group can be provided.
  • the 5-trifluoromethyl-4-nitro-2-isoxazoline compound is useful as an intermediate for producing pest control agents and functional materials such as pharmaceuticals and electronic materials.
  • “5-trifluoromethyl-4-nitro-2-isoxazoline compound” means a substituted or unsubstituted alkyl at the 3-position and 5-position of 5-trifluoromethyl-4-nitro-2-isoxazoline.
  • “4-nitro-2-isoxazoline compound” means a substituted or unsubstituted alkyl group, alkenyl group, alkynyl group, aryl group at the 3-position and 5-position of 4-nitro-2-isoxazoline. Refers to a group of compounds having
  • the 5-trifluoromethyl-4-nitro-2-isoxazoline compound according to the present invention is represented by the above general formula (1).
  • the absolute configuration of the 5-trifluoromethyl-4-nitro-2-isoxazoline compound is any of (S, S) configuration, (S, R) configuration, (R, S) configuration, and (R, R) configuration. May be. That is, stereoisomers such as optical isomers or diastereoisomers (diastereomers), and any mixtures and racemates of stereoisomers are included in the scope of the present invention.
  • examples of the substituted or unsubstituted alkyl group represented by R 1 and R 2 include, independently of each other, an alkyl group having about 1 to 20 carbon atoms. Specifically, for example, Methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl , Octadecyl group, nonadecyl group, icosyl group and the like, or these cyclic alkyl groups, branched alkyl groups and the like.
  • the alkyl group has a hydrogen atom substituted with a substituent such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group, an aryl group, an acyl group, an alkoxy group, an aryloxy group, or an acyloxy group. Also good. Moreover, when it has two or more substituents, these substituents may be the same or different from each other.
  • a substituent such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group, an aryl group, an acyl group, an alkoxy group, an aryloxy group, or an acyloxy group. Also good. Moreover, when it has two or more substituents, these substituents may be the same or different from each other.
  • examples of the substituted or unsubstituted alkenyl group or alkynyl group represented by R 1 and R 2 include, independently of each other, an alkenyl group or alkynyl group having about 2 to 20 carbon atoms.
  • the number of unsaturated bonds contained in these alkenyl groups or alkynyl groups is not particularly limited, but is preferably about one or two.
  • the alkenyl group or alkynyl group may be linear or branched.
  • the alkenyl group has a hydrogen atom substituted with a substituent such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group, an aryl group, an acyl group, an alkoxy group, an aryloxy group, or an acyloxy group. Also good. Moreover, when it has two or more substituents, these substituents may be the same or different from each other.
  • a substituent such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group, an aryl group, an acyl group, an alkoxy group, an aryloxy group, or an acyloxy group. Also good. Moreover, when it has two or more substituents, these substituents may be the same or different from each other.
  • a hydrogen atom is substituted with a substituent such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group, an aryl group, an acyl group, an alkoxy group, an aryloxy group, or an acyloxy group. It may be. Moreover, when it has two or more substituents, these substituents may be the same or different from each other.
  • the substituted or unsubstituted aryl group represented by R 1 and R 2 includes a heteroaryl group.
  • the aryl group include, independently of each other, an aryl group having 2 to 30 carbon atoms. Specific examples include a phenyl group, a naphthyl group, an anthranyl group, a pyrenyl group, a biphenyl group, an indenyl group, and a tetrahydronaphthyl group.
  • the above aryl group is substituted with a hydrogen atom by a substituent such as an alkyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group, an aryl group, an acyl group, an alkoxy group, an aryloxy group, or an acyloxy group. May be. Moreover, when it has two or more substituents, these substituents may be the same or different from each other.
  • R 1 in the general formula (1) is more preferably a methyl group, a substituted or unsubstituted vinyl group (alkenyl group), or a substituted or unsubstituted phenyl group.
  • R 2 in the general formula (1) is more preferably a methyl group or a substituted or unsubstituted phenyl group.
  • 5-trifluoromethyl-4-nitro-2-isoxazoline compounds represented by the general formula (1) 5- (trifluoromethyl) -4,5-dihydro-3-methyl-4-nitro -5-styryl-2-isoxazole, 5- (trifluoromethyl) -4,5-dihydro-3-methyl-5-((E) -2- (naphthalen-4-yl) vinyl) -4-nitro- 2-isoxazole, 5- (trifluoromethyl) -4,5-dihydro-3-methyl-5-((E) -2- (naphthalen-3-yl) vinyl) -4-nitro-2-isoxazole, 5 -(4-Methylstyryl) -5- (trifluoromethyl) -4,5-dihydro-3-methyl-4-nitro-2-isoxazole, 5- (4-methoxystyryl) -5- (trifluoromethyl) 4,5-dihydro-3-methyl-4-nitro-2-isoxazole, 5-
  • the method for producing a 5-trifluoromethyl-4-nitro-2-isoxazoline compound according to the present invention is a method for producing a 5-trifluoromethyl-4-nitro-2-isoxazoline compound represented by the general formula (1).
  • the 4-nitro-2-isoxazole compound represented by the general formula (2) is reacted with (trifluoromethyl) trimethylsilane (CF 3 SiMe 3 ).
  • the reaction is more preferably carried out in solution in the presence of a phase transfer catalyst and a base.
  • the amount of (trifluoromethyl) trimethylsilane relative to 1 mol of 4-nitro-2-isoxazole compound may be more than 0 and 1 mol or less, but in order to suppress the formation of by-products, 0.2% More preferably, it is about a mole.
  • the solvent used in the reaction is not particularly limited as long as it is a solvent in which 5-trifluoromethyl-4-nitro-2-isoxazoline compound, 4-nitro-2-isoxazole compound, and (trifluoromethyl) trimethylsilane are dissolved.
  • ether solvents such as diethyl ether, diisopropyl ether, n-butyl methyl ether, tert-butyl methyl ether, tetrahydrofuran and dioxane; hexane, heptane, cyclopentane, cyclohexane and the like
  • Hydrocarbon solvents such as: Chloroform, carbon tetrachloride, methylene chloride, dichloroethane, trichloroethane, and other halogenated hydrocarbon solvents; benzene, toluene, xylene, cumene, cymene, mesitylene, diisopropylbenzene, pyridine, pyrimidine, Aromatic solvents such as pyrazine and pyridazine; alcohol solvents such as methanol, ethanol, propanol, iso-propyl alcohol, aminoethanol, N, N-dimethyla
  • the concentration of the 4-nitro-2-isoxazole compound in the solution is not particularly limited, although a higher concentration is preferable because it is more efficient.
  • the phase transfer catalyst used in the reaction is not particularly limited.
  • a salt that generates a long-chain alkylammonium cation that is, tetraethylammonium salt, tetrapropylammonium salt, tetrabutylammonium salt
  • Examples include octylmethylammonium salt, benzyltrimethylammonium salt, benzyltriethylammonium salt, benzyldimethyloctadecylammonium salt, benzyltributylammonium salt, decyltrimethylammonium salt, cetyltrimethylammonium salt, and cetyltriethylammonium salt.
  • Examples of atoms that generate a counter anion include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • atoms that generate a counter anion include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • cetyltrimethylammonium salt and cetyltriethylammonium salt are most preferred, and among the phase transfer catalysts, cetyltrimethylammonium bromide is most preferred.
  • the amount of the phase transfer catalyst relative to the 4-nitro-2-isoxazole compound may be more than 0 and not more than 1 equivalent.
  • Examples of the base used in the reaction include inorganic bases, organic bases, organometallic reagents, and the like. Specific examples include carbonates such as potassium carbonate and cesium carbonate; acetates such as sodium acetate and potassium acetate; tetramethylammonium.
  • Ammonium fluoride such as fluoride, tetraethylammonium fluoride, tetrabutylammonium fluoride; alkali metal fluorides such as potassium fluoride and cesium fluoride; hydroxide such as sodium hydroxide and potassium hydroxide; sodium methoxide Alkoxide compounds such as potassium tert-butoxide; organic bases such as DABCO (1,4-diazabicyclo [2.2.2] octane), DBU (diazabicycloundecene), triethylamine, N, N-dimethylaminopyridine; n-butyllithium, sec-butyllithium, tert- Butyllithium, lithium diisopropylamide, lithium salts such as hexamethyldisilazane lithium salt; and the like.
  • sodium acetate is most preferred.
  • the amount of the base relative to the 4-nitro-2-isoxazole compound may be 1 to 10 equivalents, and preferably 1.5 equivalents.
  • the reactor is not particularly limited, and any of a reactor open to the atmosphere and a sealed reactor such as an autoclave can be used.
  • the order (timing) of 4-nitro-2-isoxazole compound, (trifluoromethyl) trimethylsilane, phase transfer catalyst, and base added to the solvent is not particularly limited, but a by-product is generated. In order to suppress this, it is more preferable to add (trifluoromethyl) trimethylsilane to a solution containing a 4-nitro-2-isoxazole compound, a phase transfer catalyst, and a base.
  • the reaction temperature is not particularly limited, but is usually ⁇ 80 ° C. to 120 ° C., more preferably around room temperature (25 ° C.).
  • the reaction pressure may be either atmospheric pressure or pressurized.
  • the reaction time is not particularly limited, but the reaction is usually completed in 3 to 9 hours.
  • the 4-nitro-2-isoxazole compound is substituted at the 5-position with trifluoromethyl.
  • a trifluoromethyl anion which is a fluorinating reagent, a novel compound group of 5-trifluoromethyl-4-nitro-2-isoxazoline compounds can be obtained.
  • the method for isolating and purifying the 5-trifluoromethyl-4-nitro-2-isoxazoline compound from the reaction solution after acid treatment as necessary is not particularly limited, and a general method is used. Can be adopted. Specifically, for example, after concentrating the reaction solution, purification by column chromatography using an adsorbent such as silica gel, alumina, zeolite, salting out, recrystallization and the like can be mentioned.
  • the 4-nitro-2-isoxazole compound (0.20 mmol) represented by the general formula (2), cetyltrimethylammonium bromide (21.9 mg, 0.06 mmol) as a phase transfer catalyst, and Sodium acetate (24.6 mg, 0.30 mmol) was dissolved in 1 mL of dimethylformamide as a solvent. To the resulting solution was added (trifluoromethyl) trimethylsilane (59.1 ⁇ L, 0.04 mmol) at room temperature. Thereafter, the reaction solution was stirred at room temperature for 3 to 9 hours to react the 4-nitro-2-isoxazole compound with (trifluoromethyl) trimethylsilane.
  • the 5-trifluoromethyl-4-nitro-2-isoxazoline compound according to the present invention is useful as an intermediate for producing pesticides and functional materials such as pharmaceuticals and electronic materials.
  • the production method according to the present invention is useful because it can produce a pesticide and a production intermediate of a functional material such as a pharmaceutical or an electronic material.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne : un procédé de synthèse de 5-trifluorométhyl-4-nitro-2-isoxazolines par trifluorométhylation directe; et les composés correspondants. Les 5-trifluorométhyl-4-nitro-2-isoxazolines de formule générale (1) sont synthétisées par réaction d'un 4-nitro-2-isoxazole avec le (trifluorométhyl)triméthylsilane, préférentiellement dans un solvant en présence d'un catalyseur de transfert de phase et d'une base, suivie d'un traitement acide le cas échéant. Dans la formule générale (1), chacun des radicaux R1 et R2 représente indépendamment un groupement alkyle, alcényle, alcynyle ou aryle, chacun étant éventuellement substitué.
PCT/JP2011/074346 2010-11-02 2011-10-21 5-trifluorométhyl-4-nitro-2-isoxazolines et leur procédé de synthèse Ceased WO2012060232A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN2011800512540A CN103180303A (zh) 2010-11-02 2011-10-21 5-三氟甲基-4-硝基-2-异噁唑啉化合物及其制造方法
IL225915A IL225915A0 (en) 2010-11-02 2013-04-23 5-trifluoromethyl-4-nitro-2-isoxazoline compounds and their preparation process

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JP2010-246326 2010-11-02
JP2010246326 2010-11-02

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WO2014024752A1 (fr) * 2012-08-07 2014-02-13 国立大学法人名古屋工業大学 Dérivé de 5-trifluorométhyl-4-trifluorométhylsulfonyl-2-isoxazoline, et procédé pour produire celui-ci
CN114790179A (zh) * 2022-03-24 2022-07-26 山东理工大学 一种含硫2，4，5-三取代噁唑类化合物及其制备方法和应用
CN117964570A (zh) * 2024-01-30 2024-05-03 湖南省第二测绘院 一种光介导绿色高效合成农药分子中间体异噁唑（啉）的方法

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CN105622536B (zh) * 2015-12-30 2018-06-29 商丘师范学院 一种三氟甲基化烯基异噁唑化合物及其制备方法和应用
CN106625892A (zh) * 2016-11-08 2017-05-10 广西罗城新科双全有机食品有限公司 一种电链锯

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014024752A1 (fr) * 2012-08-07 2014-02-13 国立大学法人名古屋工業大学 Dérivé de 5-trifluorométhyl-4-trifluorométhylsulfonyl-2-isoxazoline, et procédé pour produire celui-ci
CN114790179A (zh) * 2022-03-24 2022-07-26 山东理工大学 一种含硫2，4，5-三取代噁唑类化合物及其制备方法和应用
CN114790179B (zh) * 2022-03-24 2024-05-07 山东理工大学 一种含硫2，4，5-三取代噁唑类化合物及其制备方法和应用
CN117964570A (zh) * 2024-01-30 2024-05-03 湖南省第二测绘院 一种光介导绿色高效合成农药分子中间体异噁唑（啉）的方法

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IL225915A0 (en) 2013-06-27
JP2012111745A (ja) 2012-06-14

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