CN111732555A - Synthesis method of 1, 3-oxazinone - Google Patents
Synthesis method of 1, 3-oxazinone Download PDFInfo
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- CN111732555A CN111732555A CN202010647810.1A CN202010647810A CN111732555A CN 111732555 A CN111732555 A CN 111732555A CN 202010647810 A CN202010647810 A CN 202010647810A CN 111732555 A CN111732555 A CN 111732555A
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- oxazinone
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- JVTRZJXFAOQMRA-UHFFFAOYSA-N 1,3-oxazin-2-one Chemical compound O=C1N=CC=CO1 JVTRZJXFAOQMRA-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000001308 synthesis method Methods 0.000 title abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 239000000376 reactant Substances 0.000 claims abstract description 22
- 239000003960 organic solvent Substances 0.000 claims abstract description 21
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 229910052709 silver Inorganic materials 0.000 claims abstract description 19
- 239000004332 silver Substances 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000011259 mixed solution Substances 0.000 claims abstract description 16
- 150000002923 oximes Chemical class 0.000 claims abstract description 16
- GGRQLKPIJPFWEZ-UHFFFAOYSA-N cycloprop-2-en-1-one Chemical compound O=C1C=C1 GGRQLKPIJPFWEZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 229910052786 argon Inorganic materials 0.000 claims abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 20
- 239000000741 silica gel Substances 0.000 claims description 20
- 229910002027 silica gel Inorganic materials 0.000 claims description 20
- 238000005406 washing Methods 0.000 claims description 15
- 239000003085 diluting agent Substances 0.000 claims description 10
- 239000003208 petroleum Substances 0.000 claims description 10
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 238000010790 dilution Methods 0.000 claims description 5
- 239000012895 dilution Substances 0.000 claims description 5
- 239000003480 eluent Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 229910001923 silver oxide Inorganic materials 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 claims description 3
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 claims description 3
- 229940071536 silver acetate Drugs 0.000 claims description 3
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 claims description 3
- 229910001958 silver carbonate Inorganic materials 0.000 claims description 3
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- -1 acyl ketones Chemical class 0.000 description 5
- 238000012805 post-processing Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical group O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 1
- 238000007115 1,4-cycloaddition reaction Methods 0.000 description 1
- OOHAJTLMZFITEZ-UHFFFAOYSA-N 2-diazonio-3-oxo-1,3-diphenylprop-1-en-1-olate Chemical compound C=1C=CC=CC=1C(/[O-])=C(\[N+]#N)C(=O)C1=CC=CC=C1 OOHAJTLMZFITEZ-UHFFFAOYSA-N 0.000 description 1
- XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical group OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 238000006044 Wolff rearrangement reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 description 1
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a method for synthesizing 1, 3-oxazinone, which comprises the following steps: under the protection of nitrogen or argon, oxime, cyclopropenone, a silver catalyst and an organic solvent are mixed to obtain a mixed solution, then the mixed solution is heated to 60-100 ℃, stirred and reacted for 15-24 hours at the temperature to obtain a reactant, the reactant is cooled to room temperature, and then post-treatment is carried out to obtain the 1, 3-oxazinone. The synthesis method of the 1, 3-oxazinone disclosed by the invention has the following beneficial effects: 1. the reaction steps are few; 2. the reaction yield is good; 3. the reaction condition is mild.
Description
Technical Field
The invention relates to a synthesis method of 1, 3-oxazinone, belonging to the field of organic synthesis.
Background
1, 3-oxazinones are an important class of heterocyclic compounds which have pesticidal activity and are widely used in herbicides.
One of the representative commercial pesticides containing a 1, 3-oxazolone backbone is oxazolone, which is a novel and highly effective herbicide for rice and turf. However, although the 1, 3-oxazinone derivatives have important synthetic value, the research progress of the synthetic method is relatively small. The most common method for the synthesis of 1, 3-oxazinone derivatives is the formal [4+2] cycloaddition reaction with imines using acyl ketones as intermediates. For example: the acyl ketone intermediate generated by the thermal Wolff rearrangement of the 2-diazo-1, 3-diphenylpropane-1, 3-dione and imine have a chemical specificity [2+4] coupling reaction to generate the corresponding 1, 3-oxazinone derivative. 2011 reported the preparation of an acyl ketone intermediate by pd catalyzed carbonylation of a diazoketone followed by delivery of a 1, 3-dioxin-4-1 derivative in a similar manner. In addition, the Bertolini (Bertolini) group developed a simple method for obtaining 1, 3-oxazinone derivatives in two steps. Yet another method reported by Kim (Kim) involves two steps, including a strong base catalyzed reaction of diformyl oxalate with benzyl cyanide followed by a strong acid catalyzed condensation reaction, however both methods suffer from the following disadvantages: 1. 1, multiple reaction steps are carried out; 2. the reaction yield is low; 3. the reaction conditions are severe and require the addition of strong acids or bases. Therefore, in view of these limitations and problems, development of a new process for preparing 1, 3-oxazinone derivatives remains to be improved.
Disclosure of Invention
The purpose of the invention is as follows: the invention improves the problems existing in the prior art, namely the invention discloses a method for synthesizing 1, 3-oxazinone.
The technical scheme is as follows: a method for synthesizing 1, 3-oxazinone comprises the following steps:
under the protection of nitrogen or argon, mixing oxime shown in a formula (a), cyclopropenone shown in a formula (b), a silver catalyst and an organic solvent to obtain a mixed solution, heating the mixed solution to 60-100 ℃, stirring and reacting for 15-24 hours at the temperature to obtain a reactant, cooling the reactant to room temperature, and performing post-treatment to obtain the 1, 3-oxazinone shown in the formula (c), wherein:
the ratio of the amounts of the oxime represented by the formula (a), the cyclopropenone represented by the formula (b), and the silver catalyst is: 1: (0.3-0.6): (0.06-0.6);
the volume of the organic solvent is 4-8L/mol based on the molar amount of the oxime represented by the formula (a);
in the formulae (a) and (c), R1Is one of methyl, ethyl, n-propyl, phenyl and benzyl; r2Is methyl, ethylOne of n-propyl, phenyl, benzyl, 4-methylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl, 4-trifluoromethylphenyl, 3-methylphenyl, 3-methoxyphenyl, and 3-fluorophenyl.
Further, the silver catalyst is one of silver acetate, silver carbonate, silver nitrate and silver oxide.
Further, the silver catalyst is preferably silver oxide.
Further, the organic solvent is one of cyclohexane, toluene and chloroform.
Further, the post-processing comprises the steps of:
(1) adding diethyl ether into the reactant for dilution to obtain a reaction diluent, wherein: the amount of ether added is 2 times of the volume of the reactants;
(2) filtering the reaction diluent through a silica gel pad of 300-400 meshes, washing residues on the silica gel pad with diethyl ether, and collecting a washing solution;
(3) and (3) draining the organic solvent in the washing liquid, and separating by a silica gel column to obtain the 1, 3-oxazinone shown in the formula (c).
Further, in the step (3), when the silica gel column separation is performed, a mixed solution of petroleum ether and ethyl acetate is used as an eluent, wherein:
petroleum ether: the volume ratio of ethyl acetate was 30: 1.
Has the advantages that: the synthesis method of the 1, 3-oxazinone disclosed by the invention has the following beneficial effects:
1. the reaction steps are fewer, namely a reaction system of the 1, 3-oxazinone compound is constructed in one step;
2. the reaction yield is good;
3. the reaction condition is mild.
The specific implementation mode is as follows:
the following describes in detail specific embodiments of the present invention.
Detailed description of the preferred embodiment 1
A method for synthesizing 1, 3-oxazinone comprises the following steps:
under the protection of nitrogen, mixing oxime shown in a formula (a), cyclopropenone shown in a formula (b), a silver catalyst and an organic solvent to obtain a mixed solution, heating the mixed solution to 60 ℃, stirring and reacting at the temperature for 24 hours to obtain a reactant, cooling the reactant to room temperature, and performing aftertreatment to obtain the 1, 3-oxazinone shown in the formula (c), wherein the reaction yield is 72.5 percent:
the ratio of the amounts of the oxime represented by the formula (a), the cyclopropenone represented by the formula (b), and the silver catalyst is: 1: 0.3: 0.06;
the organic solvent was used in a volume of 4L/mol based on the molar amount of the oxime represented by the formula (a);
in the formulae (a) and (c), R1Is methyl; r2Is methyl.
Further, the silver catalyst is silver acetate.
Further, the organic solvent is cyclohexane.
Further, the post-processing comprises the steps of:
(1) adding diethyl ether into the reactant for dilution to obtain a reaction diluent, wherein: the amount of ether added is 2 times of the volume of the reactants;
(2) filtering the reaction diluent through a 300-mesh silica gel pad, washing residues on the silica gel pad with diethyl ether, and collecting a washing solution;
(3) and (3) draining the organic solvent in the washing liquid, and separating by a silica gel column to obtain the 1, 3-oxazinone shown in the formula (c).
Further, in the step (3), when the silica gel column separation is performed, a mixed solution of petroleum ether and ethyl acetate is used as an eluent, wherein:
petroleum ether: the volume ratio of ethyl acetate was 30: 1.
Specific example 2
A method for synthesizing 1, 3-oxazinone comprises the following steps:
under the protection of argon, mixing oxime shown in a formula (a), cyclopropenone shown in a formula (b), a silver catalyst and an organic solvent to obtain a mixed solution, heating the mixed solution to 100 ℃, stirring and reacting at the temperature for 15 hours to obtain a reactant, cooling the reactant to room temperature, and performing aftertreatment to obtain the 1, 3-oxazinone shown in the formula (c), wherein the reaction yield is 78 percent:
the ratio of the amounts of the oxime represented by the formula (a), the cyclopropenone represented by the formula (b), and the silver catalyst is: 1: 0.6: 0.6;
the organic solvent is used in a volume of 8L/mol based on the molar amount of the oxime represented by the formula (a);
in the formulae (a) and (c), R1Is ethyl; r2Is ethyl.
Further, the silver catalyst is silver carbonate.
Further, the organic solvent is toluene.
Further, the post-processing comprises the steps of:
(1) adding diethyl ether into the reactant for dilution to obtain a reaction diluent, wherein: the amount of ether added is 2 times of the volume of the reactants;
(2) filtering the reaction diluent through a 400-mesh silica gel pad, washing residues on the silica gel pad with diethyl ether, and collecting a washing solution;
(3) and (3) draining the organic solvent in the washing liquid, and separating by a silica gel column to obtain the 1, 3-oxazinone shown in the formula (c).
Further, in the step (3), when the silica gel column separation is performed, a mixed solution of petroleum ether and ethyl acetate is used as an eluent, wherein:
petroleum ether: the volume ratio of ethyl acetate was 30: 1.
Specific example 3
A method for synthesizing 1, 3-oxazinone comprises the following steps:
under the protection of nitrogen, mixing oxime shown in a formula (a), cyclopropenone shown in a formula (b), a silver catalyst and an organic solvent to obtain a mixed solution, heating the mixed solution to 80 ℃, stirring and reacting at the temperature for 20 hours to obtain a reactant, cooling the reactant to room temperature, and performing aftertreatment to obtain the 1, 3-oxazinone shown in the formula (c), wherein the reaction yield is 88.5 percent:
the ratio of the amounts of the oxime represented by the formula (a), the cyclopropenone represented by the formula (b), and the silver catalyst is: 1: 0.45: 0.1;
the organic solvent is used in a volume of 6L/mol based on the molar amount of the oxime represented by the formula (a);
in the formulae (a) and (c), R1Is n-propyl; r2Is n-propyl.
Further, the silver catalyst is silver oxide.
Further, the organic solvent is chloroform.
Further, the post-processing comprises the steps of:
(1) adding diethyl ether into the reactant for dilution to obtain a reaction diluent, wherein: the amount of ether added is 2 times of the volume of the reactants;
(2) filtering the reaction diluent through a 325-mesh silica gel pad, washing residues on the silica gel pad with diethyl ether, and collecting a washing solution;
(3) and (3) draining the organic solvent in the washing liquid, and separating by a silica gel column to obtain the 1, 3-oxazinone shown in the formula (c).
Further, in the step (3), when the silica gel column separation is performed, a mixed solution of petroleum ether and ethyl acetate is used as an eluent, wherein:
petroleum ether: the volume ratio of ethyl acetate was 30: 1.
Specific example 4
The only difference is that the silver catalyst is silver nitrate, which is the same as in example 1.
Specific examples 5 to 17
Substantially the same as in example 3, except that R1And/or R2The substituents are different and are shown in the following table:
the embodiments of the present invention have been described in detail. However, the present invention is not limited to the above-described embodiments, and various changes can be made within the knowledge of those skilled in the art without departing from the spirit of the present invention.
Claims (6)
1. A method for synthesizing 1, 3-oxazinone is characterized in that the method comprises the following steps:
under the protection of nitrogen or argon, mixing oxime shown in a formula (a), cyclopropenone shown in a formula (b), a silver catalyst and an organic solvent to obtain a mixed solution, heating the mixed solution to 60-100 ℃, stirring and reacting for 15-24 hours at the temperature to obtain a reactant, cooling the reactant to room temperature, and performing post-treatment to obtain the 1, 3-oxazinone shown in the formula (c), wherein:
the ratio of the amounts of the oxime represented by the formula (a), the cyclopropenone represented by the formula (b), and the silver catalyst is: 1: (0.3-0.6): (0.06-0.6);
the volume of the organic solvent is 4-8L/mol based on the molar amount of the oxime represented by the formula (a);
in the formulae (a) and (c), R1Is one of methyl, ethyl, n-propyl, phenyl and benzyl; r2Is one of methyl, ethyl, n-propyl, phenyl, benzyl, 4-methylphenyl, 4-methoxyphenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl, 4-trifluoromethylphenyl, 3-methylphenyl, 3-methoxyphenyl and 3-fluorophenyl.
2. The method for synthesizing 1, 3-oxazinone as claimed in claim 1, wherein the silver catalyst is one of silver acetate, silver carbonate, silver nitrate and silver oxide.
3. A process for the synthesis of 1, 3-oxazinones according to claim 2, wherein the silver catalyst is preferably silver oxide.
4. The method for synthesizing 1, 3-oxazinone as claimed in claim 1, wherein the organic solvent is one of cyclohexane, toluene and chloroform.
5. A method of synthesizing a 1, 3-oxazinone as claimed in claim 1, wherein the post-treatment comprises the steps of:
(1) adding diethyl ether into the reactant for dilution to obtain a reaction diluent, wherein: the amount of ether added is 2 times of the volume of the reactants;
(2) filtering the reaction diluent through a silica gel pad of 300-400 meshes, washing residues on the silica gel pad with diethyl ether, and collecting a washing solution;
(3) and (3) draining the organic solvent in the washing liquid, and separating by a silica gel column to obtain the 1, 3-oxazinone shown in the formula (c).
6. The method for synthesizing 1, 3-oxazinone according to claim 5, wherein silica gel column separation in step (3) is carried out using a mixture of petroleum ether and ethyl acetate as eluent, wherein:
petroleum ether: the volume ratio of ethyl acetate was 30: 1.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1154367A (en) * | 1995-11-17 | 1997-07-16 | 田边制药株式会社 | Process for preparing acetoxyazetidinone derivative and intermediate thereof |
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2020
- 2020-07-07 CN CN202010647810.1A patent/CN111732555A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1154367A (en) * | 1995-11-17 | 1997-07-16 | 田边制药株式会社 | Process for preparing acetoxyazetidinone derivative and intermediate thereof |
Non-Patent Citations (1)
| Title |
|---|
| YE-FEI YANG等: "Ag2O-promoted ring-opening reactions of cyclopropenones with oximes", 《ORGANIC & BIOMOLECULAR CHEMISTRY》 * |
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