CN111484462A - 4-isoxazoline compound and preparation method thereof - Google Patents

4-isoxazoline compound and preparation method thereof Download PDF

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CN111484462A
CN111484462A CN202010440782.6A CN202010440782A CN111484462A CN 111484462 A CN111484462 A CN 111484462A CN 202010440782 A CN202010440782 A CN 202010440782A CN 111484462 A CN111484462 A CN 111484462A
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carbamate
hydroxy
trifluoroethyl
phenyl
methyl
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冯超
水洋
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Nanjing Tech University
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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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00

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  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

The invention discloses a 4-isoxazoline compound and a preparation method thereof.A propargyl N-hydroxylamine, triphenylphosphine gold chloride and silver trifluoromethanesulfonate are sequentially added into a solvent in an inert gas atmosphere to obtain a mixture, wherein the molar volume ratio of the propargyl N-hydroxylamine, the triphenylphosphine gold chloride, the silver trifluoromethanesulfonate to the solvent is 0.1-1 mmol, 0.005-0.05 mmol, 2m L-20 m L, and the obtained mixture is reacted for 0.5-1 h under the conditions of inert gas and room temperature to obtain the 4-isoxazoline compound.

Description

4-isoxazoline compound and preparation method thereof
Technical Field
The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a 4-isoxazoline compound and a preparation method thereof.
Background
Heterocyclic compounds as a specific organic functional skeleton widely exist in natural products and small drug molecules, and therefore, the synthesis of heterocyclic compounds is also widely concerned by organic chemists. In recent decades, the synthesis of heterocyclic compounds has been reported vigorously and has made progress, such as pyrrole, pyridine and quinoline, etc. which are nitrogen-containing heterocyclic compounds, furan, pyran, etc. which are oxygen-containing heterocyclic compounds, thiophene, etc. which is sulfur-containing heterocyclic compounds, and compounds containing two hetero atoms, such as oxazole, isoxazole, imidazole, thiazole, etc.
In the synthesis of quinoline, for example, as shown in document 1(Braun, m.; Esposito, d.chemcatchem,2016,9, 393-397.) under pressure, a substrate is reduced with hydrogen/palladium, then α -unsaturated aldehyde is attacked, and finally oxygen is removed to produce the final target product, quinoline.
Figure BDA0002503987600000011
There are also some reports on the synthesis of pyrrole, for example, in a method reported in document 2(Davies, j.; s.sheikh, n.; L eonori, d.angelw.chem.int.ed.2017, 56, 13361-:
Figure BDA0002503987600000021
the two columns of reports on the synthesis of nitrogen-containing heterocycles are good methods for synthesizing specific heterocycles, but the reports on heterocycles containing a nitrogen-oxygen double heteroatom are rare. Therefore, the development of a novel synthetic method has great significance.
In the method disclosed in document 3(Fabio, M.; Ronzini, L.; Troisi, L. Tetrahedron 2008,64, 4979-4984), a nitrogen-oxygen atom-containing 4-isoxazoline can be obtained by using a nitrogen-oxygen atom-containing three-membered ring as a substrate and a terminal alkyne under the condition of heating and refluxing, and the specific reaction process is as follows:
Figure BDA0002503987600000022
the method does not need to add extra catalyst, and the target product can be obtained by the reaction of the two components under the condition of heating and refluxing. However, this reaction has a disadvantage in that severe reaction conditions such as high-temperature reflux are required.
Many drug molecules contain azacyclo compounds, such as cloxacillin for treating septicemia, soft tissue infection, dicloxacillin for treating staphylococcus infection, and danazol for treating endometriosis. Therefore, the synthesis of cyclic compounds containing a nitrogen oxygen heteroatom is of great significance.
Disclosure of Invention
The invention aims at providing a 4-isoxazoline compound.
Still another object of the present invention is to provide a method for preparing the above 4-isoxazoline compound, which has the characteristics of simple and easily available raw materials, wide substrate range, mild reaction conditions, very small amount of required catalyst, low cost, high reaction efficiency, and the like.
The invention is realized by the following steps that a 4-isoxazoline compound has a chemical structural formula shown as the following formula (I):
Figure BDA0002503987600000023
in the above formula (I), R1Is any one of trifluoroethoxycarbonyl, trichloroethoxycarbonyl, benzyloxycarbonyl, tert-butoxycarbonyl and benzoyl;
R2is any one of phenyl, isopropyl, 4-methylphenyl, 4-methoxyphenyl, 4-phenylphenyl, 4-trifluoromethoxyphenyl, 4-fluorophenyl, 4-chlorphenyl, naphthyl, 2, 3-dihydrobenzofuran, benzofuran, thiophene and benzothiophene;
R3is any one of phenyl 4-methylphenyl, 3-methoxyphenyl, 4-phenylphenyl, 4-fluorophenyl, 3-chlorophenyl, n-propyl, cyclopropyl, tert-butyl, phenethyl, cyclohexylmethyl and n-decyl.
The invention further discloses a preparation method of the 4-isoxazoline compound, which comprises the following steps:
(1) under the inert gas atmosphere, sequentially adding propargyl N-hydroxylamine, triphenylphosphine gold chloride and silver trifluoromethanesulfonate into a solvent to obtain a mixture, wherein the molar volume ratio of the propargyl N-hydroxylamine, the triphenylphosphine gold chloride, the silver trifluoromethanesulfonate to the solvent is 0.1-1 mmol, 0.005-0.05 mmol, 2m L-20 m L;
(2) and (2) reacting the mixture obtained in the step (1) for 0.5-1 h under the conditions of inert gas and room temperature to obtain the 4-isoxazoline compound.
Preferably, in step (1), the propargyl N-hydroxylamine is 2,2, 2-trifluoroethyl (1, 3-diphenylpropyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethyl hydroxy (1-phenyl-3- (p-tolyl) propyl-2-yn-1-yl) carbamate, 2,2, 2-trifluoroethyl hydroxy (3- (3-methoxyphenyl) -1-phenylpropyl-2-yn-1-yl) carbamate, 2,2, 2-trifluoroethyl (3- ([1,1' -biphenyl ] -4-yl) -1-phenylpropyl-2-yn-1-yl) (hydroxy) carbamate, or a salt thereof, 2,2, 2-trifluoroethyl (3- (4-fluorophenyl) -1-phenylpropyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethyl (3- (3-chlorophenyl) -1-phenyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethylhydroxy (1-phenylhexyl-2-yn-1-yl) carbamate, 2,2, 2-trifluoroethyl (3-cyclopropyl-1-phenyl-2-yn-1-yl) (hydroxy) carbamate Acid esters, 2,2, 2-trifluoroethyl (4, 4-dimethyl-1-phenylpent-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethyl (1, 5-diphenyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethyl (4-cyclohexyl-1-phenyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethylhydroxy (1-phenyltridecyl-2-yn-1-yl) carbamate, 2,2, 2-trifluoroethylhydroxy (3-phenyl-1- (p-tolyl) propyl-2-yn-1-yl) carbamate, di-or tri-fluoro-ethyl (4-cyclohexyl-1-phenyl-2-yn-1-yl) (hydroxy) carbamate, di-or tri-fluoro-ethyl (2-phenyl-1- (p-tolyl) propyl-2-yn-1-, 2,2, 2-trifluoroethylhydroxy (1- (4-methoxyphenyl) -3-phenylpropyl-2-yn-1-yl) carbamate, 2,2, 2-trifluoroethyl (1- ([1,1' -biphenyl ] -4-yl) -3-phenylpropyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethylhydroxy (3-phenyl-1- (4- (trifluoromethoxy) phenyl) propyl-2-yn-1-yl) carbamate, 2,2, 2-trifluoroethyl (1- (4-chlorophenyl) -3-phenyl-2-yn-1-yl) (hydroxy) carbamate, and, 2,2, 2-trifluoroethyl (1- (4-fluorophenyl) -3-phenylpropyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethylhydroxy (1- (naphthalen-2-yl) -3-phenylpropyl-2-yn-1-yl) carbamate, 2,2, 2-trifluoroethyl (1- (2, 3-dihydrobenzofuran-5-yl) -3-phenylpropyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethylhydroxy (3-phenyl-1- (thiophen-2-yl) propyl-2-yn-1-yl) carbamate, 2-methyl-ethyl-1-yl) carbamate, methyl-ethyl-2, 2-methyl-ethyl-2-methyl-1-phenyl-2-yn-1-yl) carbamate, methyl-ethyl-2, 2-, 2,2, 2-trifluoroethyl (1- (benzothien-2-yl) -3-phenylprop-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethyl (1- (benzofuran-2-yl) -3-phenylprop-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trichloroethyl (1, 3-diphenylpropyl-2-yn-1-yl) (hydroxy) carbamate, benzyl (1, 3-diphenylpropyl-2-yn-1-yl) (hydroxy) carbamate, tert-butyl (1, 3-diphenylpropyl-2-yn-1-yl) (hydroxy) carbamate and N-hydroxy-N- (2- At least one of methyl-4-yn-3-yl) benzamides.
Preferably, in step (1), the solvent is toluene.
Preferably, in the step (1) and the step (2), the inert gas is nitrogen.
Preferably, in step (2), the reaction time is 1 h.
The invention overcomes the defects of the prior art and provides a 4-isoxazoline compound and a preparation method thereof, propargyl N-hydroxylamine is used as a reaction substrate, triphenylgold chloride is coordinated with trifluoromethanesulfonic acid group in silver trifluoromethanesulfonate, the coordinated gold catalyst is coordinated with alkyne in propargyl N-hydroxylamine to generate a transition state, then oxygen attacks alkyne to form a five-membered ring intermediate, trifluoromethanesulfonic acid group and hydrogen ion are removed to generate an intermediate with gold inserted into alkene, and the intermediate is decomposed in situ with the aid of trifluoromethanesulfonic acid to generate the final target product 4-isoxazoline.
Compared with the defects and shortcomings of the prior art, the invention has the following beneficial effects: the preparation method has the advantages of simple and easily obtained reaction raw materials, wide substrate range, mild reaction conditions, low cost and high reaction efficiency, and only uses a small amount of catalyst.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
(1) Under a nitrogen atmosphere, 0.1mmol of 2,2, 2-trifluoroethyl (1, 3-diphenylpropyl-2-yn-1-yl) (hydroxy) carbamate, 0.005mmol of triphenylphosphine gold chloride and 0.005mmol of silver trifluoromethanesulfonate were sequentially added to 2m L of toluene to obtain a mixture;
(2) reacting the mixture obtained in the step (1) for 1 hour at room temperature under a nitrogen atmosphere, and collecting the 4-isoxazoline 1 from the reaction product.
Example 2
(1) Under a nitrogen atmosphere, 0.1mmol of 2,2, 2-trifluoroethylhydroxy (1-phenyl-3- (p-tolyl) propyl-2-yn-1-yl) carbamate, 0.005mmol of triphenylphosphine gold chloride and 0.005mmol of silver trifluoromethanesulfonate were sequentially added to 2m L of toluene to obtain a mixture;
(2) reacting the mixture obtained in the step (1) for 1 hour at room temperature under a nitrogen atmosphere, and collecting the 4-isoxazoline 2 from the reaction product.
Example 3
(1) Under a nitrogen atmosphere, 0.1mmol of 2,2, 2-trifluoroethylhydroxy (3- (3-methoxyphenyl) -1-phenylpropyl-2-yn-1-yl) carbamate, 0.005mmol of triphenylphosphine gold chloride and 0.005mmol of silver trifluoromethanesulfonate were sequentially added to toluene of 2m L to obtain a mixture;
(2) reacting the mixture obtained in the step (1) for 1 hour at room temperature under a nitrogen atmosphere, and collecting the 4-isoxazoline 3 from the reaction product.
Examples 4 to 28
Examples 4-28 are essentially the same as example 1, except as shown in Table 1 below:
TABLE 1
Figure BDA0002503987600000061
Example 29
(1) Under a nitrogen atmosphere, 1mmol of 2,2, 2-trifluoroethyl (1, 3-diphenylpropyl-2-yn-1-yl) (hydroxy) carbamate, 0.005mmol of triphenylphosphine gold chloride and 0.05mmol of silver trifluoromethanesulfonate were sequentially added to toluene of 20m L to obtain a mixture;
(2) reacting the mixture obtained in the step (1) at room temperature for 0.5 hour under a nitrogen atmosphere, and collecting the 4-isoxazoline 1 from the reaction product.
Example 30
(1) Under a nitrogen atmosphere, 0.1mmol of 2,2, 2-trifluoroethyl (1, 3-diphenylpropyl-2-yn-1-yl) (hydroxy) carbamate, 0.05mmol of triphenylphosphine gold chloride and 0.005mmol of silver trifluoromethanesulfonate were sequentially added to 2m L of toluene to obtain a mixture;
(2) reacting the mixture obtained in the step (1) for 1 hour at room temperature under a nitrogen atmosphere, and collecting the 4-isoxazoline 1 from the reaction product.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.

Claims (6)

1. A4-isoxazoline compound is characterized in that the chemical structural formula of the compound is shown as the following formula (I):
Figure FDA0002503987590000011
in the above formula (I), R1Is any one of trifluoroethoxycarbonyl, trichloroethoxycarbonyl, benzyloxycarbonyl, tert-butoxycarbonyl and benzoyl;
R2is any one of phenyl, isopropyl, 4-methylphenyl, 4-methoxyphenyl, 4-phenylphenyl, 4-trifluoromethoxyphenyl, 4-fluorophenyl, 4-chlorphenyl, naphthyl, 2, 3-dihydrobenzofuran, benzofuran, thiophene and benzothiophene;
R3is any one of phenyl 4-methylphenyl, 3-methoxyphenyl, 4-phenylphenyl, 4-fluorophenyl, 3-chlorophenyl, n-propyl, cyclopropyl, tert-butyl, phenethyl, cyclohexylmethyl and n-decyl.
2. The method for producing a 4-isoxazoline compound according to claim 1, which comprises the steps of:
(1) under the inert gas atmosphere, sequentially adding propargyl N-hydroxylamine, triphenylphosphine gold chloride and silver trifluoromethanesulfonate into a solvent to obtain a mixture, wherein the molar volume ratio of the propargyl N-hydroxylamine, the triphenylphosphine gold chloride, the silver trifluoromethanesulfonate to the solvent is 0.1-1 mmol, 0.005-0.05 mmol, 2m L-20 m L;
(2) and (2) reacting the mixture obtained in the step (1) for 0.5-1 h under the conditions of inert gas and room temperature to obtain the 4-isoxazoline compound.
3. The method for producing a 4-isoxazoline compound according to claim 2, wherein in step (1), the propargyl N-hydroxylamine is 2,2, 2-trifluoroethyl (1, 3-diphenylpropyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethyl hydroxy (1-phenyl-3- (p-tolyl) propyl-2-yn-1-yl) carbamate, 2,2, 2-trifluoroethyl hydroxy (3- (3-methoxyphenyl) -1-phenylpropyl-2-yn-1-yl) carbamate, 2,2, 2-trifluoroethyl (3- ([1,1' -biphenyl ] -4-yl) -1-phenylpropyl-2-yn-1-yl) -yl) (hydroxy) carbamate, 2,2, 2-trifluoroethyl (3- (4-fluorophenyl) -1-phenylpropyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethyl (3- (3-chlorophenyl) -1-phenyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethyl hydroxy (1-phenylhexyl-2-yn-1-yl) carbamate, 2,2, 2-trifluoroethyl (3-cyclopropyl-1-phenyl-2-yn-1-yl) carbamate -1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethyl (4, 4-dimethyl-1-phenylpent-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethyl (1, 5-diphenyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethyl (4-cyclohexyl-1-phenyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethylhydroxy (1-phenyltridecyl-2-yn-1-yl) carbamate, 2,2, 2-trifluoroethylhydroxy (3-phenyl-1- (p-tolyl) propyl-2-yn-1-yl) carbamate, methyl-1-ethyl-propyl-2-yn-1-yl) carbamate, methyl-ethyl-1-yl-hydroxy, methyl-ethyl-1-, 2,2, 2-trifluoroethylhydroxy (1- (4-methoxyphenyl) -3-phenylpropyl-2-yn-1-yl) carbamate, 2,2, 2-trifluoroethyl (1- ([1,1' -biphenyl ] -4-yl) -3-phenylpropyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethylhydroxy (3-phenyl-1- (4- (trifluoromethoxy) phenyl) propyl-2-yn-1-yl) carbamate, 2,2, 2-trifluoroethyl (1- (4-chlorophenyl) -3-phenyl-2-yn-1-yl) (hydroxy) carbamate, and, 2,2, 2-trifluoroethyl (1- (4-fluorophenyl) -3-phenylpropyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethylhydroxy (1- (naphthalen-2-yl) -3-phenylpropyl-2-yn-1-yl) carbamate, 2,2, 2-trifluoroethyl (1- (2, 3-dihydrobenzofuran-5-yl) -3-phenylpropyl-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethylhydroxy (3-phenyl-1- (thiophen-2-yl) propyl-2-yn-1-yl) carbamate, 2-methyl-ethyl-1-yl) carbamate, methyl-ethyl-2, 2-methyl-ethyl-2-methyl-1-phenyl-2-yn-1-yl) carbamate, methyl-ethyl-2, 2-, 2,2, 2-trifluoroethyl (1- (benzothien-2-yl) -3-phenylprop-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trifluoroethyl (1- (benzofuran-2-yl) -3-phenylprop-2-yn-1-yl) (hydroxy) carbamate, 2,2, 2-trichloroethyl (1, 3-diphenylpropyl-2-yn-1-yl) (hydroxy) carbamate, benzyl (1, 3-diphenylpropyl-2-yn-1-yl) (hydroxy) carbamate, tert-butyl (1, 3-diphenylpropyl-2-yn-1-yl) (hydroxy) carbamate and N-hydroxy-N- (2- At least one of methyl-4-yn-3-yl) benzamides.
4. The method for producing a 4-isoxazoline compound according to claim 2, wherein in step (1), the solvent is toluene.
5. The method for producing a 4-isoxazoline compound according to claim 2, wherein the inert gas is nitrogen in the step (1) and the step (2).
6. The method for producing a 4-isoxazoline compound according to claim 2, wherein the reaction time in step (2) is 1 hour.
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Application publication date: 20200804