CN107628979A - Method for synthesizing 2H-azacyclo acrylamide - Google Patents
Method for synthesizing 2H-azacyclo acrylamide Download PDFInfo
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- CN107628979A CN107628979A CN201711024172.2A CN201711024172A CN107628979A CN 107628979 A CN107628979 A CN 107628979A CN 201711024172 A CN201711024172 A CN 201711024172A CN 107628979 A CN107628979 A CN 107628979A
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- China
- Prior art keywords
- amido
- isoxazoles
- phenyl
- synthesis
- acid amides
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Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 title 1
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 5
- 238000005286 illumination Methods 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- -1 3- octyl groups Chemical group 0.000 claims description 21
- 238000003786 synthesis reaction Methods 0.000 claims description 17
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 238000004440 column chromatography Methods 0.000 claims description 8
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 7
- 125000003963 dichloro group Chemical group Cl* 0.000 claims description 7
- 235000019441 ethanol Nutrition 0.000 claims description 7
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 7
- 229910052707 ruthenium Inorganic materials 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 240000002853 Nelumbo nucifera Species 0.000 claims description 4
- 235000006508 Nelumbo nucifera Nutrition 0.000 claims description 4
- 235000006510 Nelumbo pentapetala Nutrition 0.000 claims description 4
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- GHPHCACQRYSXSS-UHFFFAOYSA-N ruthenium;tricyclohexylphosphane Chemical compound [Ru].C1CCCCC1P(C1CCCCC1)C1CCCCC1 GHPHCACQRYSXSS-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- QLSWIGRIBOSFMV-UHFFFAOYSA-N 1h-pyrrol-2-amine Chemical class NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 claims 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical class BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract description 4
- 150000001412 amines Chemical class 0.000 abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 125000002252 acyl group Chemical class 0.000 abstract description 2
- 150000001336 alkenes Chemical class 0.000 abstract description 2
- 150000001408 amides Chemical class 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 239000007810 chemical reaction solvent Substances 0.000 abstract 2
- IAXWZYXUKABJAN-UHFFFAOYSA-N 1,2-oxazol-5-amine Chemical compound NC1=CC=NO1 IAXWZYXUKABJAN-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract 1
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000012544 monitoring process Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229930014626 natural product Natural products 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SZTRCMOSUUQMBM-UHFFFAOYSA-N 2h-azepine Chemical class C1C=CC=CC=N1 SZTRCMOSUUQMBM-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 150000001875 compounds Chemical class 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
- 230000007812 deficiency Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention relates to a method for synthesizing 2H-azacyclo-acrylamide, which comprises the steps of adding 5-aminoisoxazole raw materials into a reaction solvent, adding a Holovad-Glabra catalyst, carrying out catalytic reaction under green light illumination, removing the reaction solvent from the obtained reaction liquid, and then purifying to obtain the product. The synthesis method of the invention has the advantages of very mild and green conditions, high yield and wide applicable substrate range, for example, 2-bit of the three-membered ring of the 2H-azaenamide can be various substituted phenyl, heterocyclic ring, olefin and alkane, 3-bit can be methyl, allyl, phenyl and 1-phenylallyl, and the amide can be substituted by aromatic hydrocarbon substituted amine, alkane and acyl.
Description
Technical field
The present invention relates to a kind of method of synthesis 2H- aziridine amide derivatives, belong to methodology of organic synthesis skill
Art field.
Background technology
2H- aziridine structures in 2H- aziridine amide derivatives are present in many natural products, are very
The common skeleton of more raw natural products medicines.Such as：
2H- aziridines have highly reactive compound as one kind, in many natural products and medicine
There is its structure.In organic synthesis, 2H- aziridines can be used as reaction intermediate, reacting precursor can also be used as to close
Into various useful heterocyclic compounds, such as pyridines, furans, pyroles, Benzazole compounds.Synthesis 2H- azepines at present
Cyclopropylene acid amides mainly has three methods, ultraviolet lighting, high-temperature heating, frerrous chloride catalysis isoxazole contracting ring.Use ultraviolet lighting
Method synthesizes 2H- aziridines, and yield is very low, and substrate spectrum applicatory is small；With high-temperature heating method synthesis 2H- azacyclo-s third
Alkene is, it is necessary to higher temperature, and generally at 100 DEG C -300 DEG C, substrate spectrum applicatory is small；Contracted with frerrous chloride catalysis isoxazole
Cyclization is into 2H- aziridines, although yield is higher, substrate spectrum very little applicatory.
The content of the invention
A kind of purpose of synthesis of the present invention is that solve the deficiencies in the prior art, there is provided one kind synthesis 2H- aziridine acyls
The method of amine, this method mild condition, suitable substrates scope is wide, and high income.
Technical scheme
A kind of method of synthesis 2H- aziridine acid amides：5- amido isoxazole raw materials are added in reaction dissolvent, then
Lotus Victor-Ge Labu catalyst is added, catalytic reaction is carried out in green glow illumination, obtained reaction solution is removed after reaction dissolvent again
Purified, produced.
Further, it is different to be selected from the iso- 5- amino oxazole of 3- octyl groups, 3- cyclohexyl -5- amino for the 5- amido isoxazoles raw material
Dislike
Azoles, 3- phenylpropyl -5- amido isoxazoles, 3- cinnamyl -5- amido isoxazoles, 3- phenyl -5- amido isoxazoles, 3-
(4- chlorphenyls) -5- amido isoxazoles, 3- (4- bromophenyls) -5- amido isoxazoles, 3- (2- naphthyls) -5- amido isoxazoles, 3-
(2- furyls) -5- amido isoxazoles, 3- phenyl -4- pi-allyl -5- amido isoxazoles, 3- phenyl -4- (1- phenyl allyls) -
It is any in 5- amido isoxazoles, 3- phenyl -5- (N- benzylaminos) isoxazoles or 3- phenyl -5- (N- octyl aminos) isoxazole
It is a kind of.
Further, the reaction dissolvent is selected from absolute ethyl alcohol, acetonitrile, 1,2- dichloroethanes, dichloromethane, toluene or isopropyl
Any one in alcohol.Preferably absolute ethyl alcohol.
Further, the lotus Victor-Ge Labu catalyst is dichloro (adjacent isopropoxy benzene methylene) (thricyclohexyl
Phosphine) ruthenium or dichloro [double (2- the aminomethyl phenyls) -2- imidazolidines subunits of 1,3-] (2- isopropoxies benzylidene) ruthenium.
Further, the catalytic reaction is carried out under 36w green light lamps, a length of 24-72h during reaction.
Further, the method for removing reaction dissolvent is to use vacuum rotary evaporator.
Further, using column chromatography, solvent is dichloromethane/ethyl acetate=4 for the purifying：1.
The beneficial effects of the invention are as follows：Condition required for the synthetic method of the present invention is very gentle, green, and yield
Height, applicable substrate spectrum is extensive, as 2 of the three-membered ring of 2H- azepine acrylamides can be various substituted-phenyls, heterocycle, alkene
Hydrocarbon, alkane, 3 can be methyl, pi-allyl, phenyl, 1- phenyl allyls, and acid amides can substitute amine, alkane substitution, acyl with aromatic hydrocarbons
Base substitutes.
Brief description of the drawings
Fig. 1 is the proton nmr spectra of 3- cyclohexyl -5- amido isoxazoles；
Fig. 2 is the carbon-13 nmr spectra of 3- cyclohexyl -5- amido isoxazoles；
Fig. 3 is the proton nmr spectra of 2- cyclohexyl -2H- aziridine acid amides made from embodiment 1；
Fig. 4 is the carbon-13 nmr spectra of 2- cyclohexyl -2H- aziridine acid amides made from embodiment 1.
Embodiment
The present invention is described in detail with reference to the accompanying drawings and detailed description.
Embodiment 1
The first step, synthesis material 3- cyclohexyl -5- amido isoxazoles：
Sodium acetate (2mmol) and hydroxylamine hydrochloride (2mmol) are added in 10ml reaction tubes, 1ml methanol is added, stirs
A hour is mixed, then adds methanol (1ml) solution of cyclohexyl formoxyl acetonitrile (1mmol), stirs 12-24h.
After TLC monitoring reactions completely, reaction solution is transferred in 100ml round-bottomed flasks, methanol is removed with vacuum rotary evaporator, adds
Water 20ml, it is extracted with ethyl acetate three times, use ethyl acetate 10ml every time, merging organic layer, with 20ml saturated common salt water washings,
Organic layer anhydrous sodium sulfate drying, ethyl acetate, column chromatography separation product, solvent pole are removed with vacuum rotary evaporator
Property petrol ether/ethyl acetate=4：1, product is faint yellow solid, yield 80%.
The proton nmr spectra of 3- cyclohexyl -5- amido isoxazoles is shown in Fig. 1, the nuclear-magnetism of 3- cyclohexyl -5- amido isoxazoles
Resonance carbon spectrum is shown in Fig. 2.
Second step, synthesize 2- cyclohexyl -2H- aziridine acid amides：
3- cyclohexyl -5- amido isoxazoles (1mmol) are added in 10ml reaction tubes, add absolute ethyl alcohol 2ml, add two
Chlorine [1,3- double (2- aminomethyl phenyls) -2- imidazolidines subunits] (2- isopropoxies benzylidene) ruthenium (1mol%), with 36W green light lamps
Irradiation 48 hours, after TLC monitoring reactions completely, reaction solution is transferred in 100ml round-bottomed flasks, removed with vacuum rotary evaporator
Ethanol, column chromatography separation product are removed, solvent is dichloromethane/ethyl acetate=4：1, product is white solid, yield
95%.
The proton nmr spectra of obtained product 2- cyclohexyl -2H- aziridine acid amides is shown in Fig. 3,2- cyclohexyl -2H-
The carbon-13 nmr spectra of aziridine acid amides is shown in Fig. 4.
Embodiment 2
3- phenylpropyl -5- amido isoxazoles (1mmol) are added in 10ml reaction tubes, add absolute ethyl alcohol 2ml, add two
Chlorine (adjacent isopropoxy benzene methylene) (tricyclohexyl phosphine) ruthenium (1mol%), with 36W green glows light irradiation 36 hours, TLC monitorings
After reaction completely, reaction solution is transferred in 100ml round-bottomed flasks, ethanol, column chromatography point are removed with vacuum rotary evaporator
From product, solvent is dichloromethane/ethyl acetate=4：1, product is white solid, yield 89%.
Embodiment 3
3- (4- chlorphenyls) isoxazole (1mmol) is added in 10ml reaction tubes, adds absolute ethyl alcohol 2ml, adds dichloro
[1,3- double (2- aminomethyl phenyls) -2- imidazolidines subunits] (2- isopropoxies benzylidene) ruthenium (1mol%), is shone with 36W green light lamps
Penetrate 32 hours, after TLC monitoring reactions completely, reaction solution is transferred in 100ml round-bottomed flasks, removed with vacuum rotary evaporator
Ethanol, column chromatography separation product, solvent are dichloromethane/ethyl acetate=4：1, product is white solid, yield 92%.
Embodiment 4
3- phenyl -4- pi-allyl -5- amido isoxazoles (1mmol) are added in 10ml reaction tubes, add dichloromethane
2ml, dichloro [1,3- double (2- aminomethyl phenyls) -2- imidazolidines subunits] (2- isopropoxies benzylidene) ruthenium (1mol%) is added,
With 36W green glows light irradiation 40 hours, after TLC monitoring reactions completely, reaction solution is transferred in 100ml round-bottomed flasks, uses vacuum
Rotary evaporator removes ethanol, and column chromatography separation product, solvent is dichloromethane/ethyl acetate=4：1, product is white
Solid, yield 87%.
Embodiment 5
3- phenyl -5- (N- benzylaminos) isoxazole (1mmol) is added in 10ml reaction tubes, adds absolute ethyl alcohol 2ml,
Dichloro [1,3- double (2- aminomethyl phenyls) -2- imidazolidines subunits] (2- isopropoxies benzylidene) ruthenium (1mol%) is added, uses 36W
Green glow light irradiation 30 hours, after TLC monitoring reactions completely, reaction solution is transferred in 100ml round-bottomed flasks, steamed with vacuum rotating
Send out device and remove ethanol, column chromatography separation product, solvent is dichloromethane/ethyl acetate=4：1, product is white solid,
Yield 90%.
Claims (7)
- A kind of 1. method of synthesis 2H- aziridine acid amides, it is characterised in that 5- amido isoxazole raw materials are added to reaction In solvent, lotus Victor-Ge Labu catalyst is added, catalytic reaction is carried out in green glow illumination, obtained reaction solution is removed anti- Purified, produced again after answering solvent.
- 2. the method for synthesis 2H- aziridine acid amides as claimed in claim 1, it is characterised in that the different evil of 5- amino Azoles raw material is selected from the iso- 5- amino oxazole of 3- octyl groups, 3- cyclohexyl -5- amido isoxazoles, 3- phenylpropyl -5- amido isoxazoles, 3- Cinnamyl -5- amido isoxazoles, 3- phenyl -5- amido isoxazoles, 3- (4- chlorphenyls) -5- amido isoxazoles, 3- (4- bromobenzenes Base) -5- amido isoxazoles, 3- (2- naphthyls) -5- amido isoxazoles, 3- (2- furyls) -5- amido isoxazoles, 3- phenyl -4- Pi-allyl -5- amido isoxazoles, 3- phenyl -4- (1- phenyl allyls) -5- amido isoxazoles, 3- phenyl -5- (N- benzyl ammonia Base) any one in isoxazole or 3- phenyl -5- (N- octyl aminos) isoxazole.
- 3. the method for synthesis 2H- aziridine acid amides as claimed in claim 1, it is characterised in that the reaction dissolvent choosing From any one in absolute ethyl alcohol, acetonitrile, 1,2- dichloroethanes, dichloromethane, toluene or isopropanol.Preferably anhydrous second Alcohol.
- 4. the method for synthesis 2H- aziridine acid amides as claimed in claim 1, it is characterised in that the lotus Victor-Ge La Cloth catalyst be dichloro (adjacent isopropoxy benzene methylene) (tricyclohexyl phosphine) ruthenium or dichloro [1,3- double (2- aminomethyl phenyls)- 2- imidazolidines subunit] (2- isopropoxies benzylidene) ruthenium.
- 5. the method for synthesis 2H- aziridine acid amides as claimed in claim 1, it is characterised in that the catalytic reaction is Carried out under 36w green light lamps, a length of 24-72h during reaction.
- 6. the method for synthesis 2H- aziridine acid amides as claimed in claim 1, it is characterised in that described except dereaction is molten The method of agent is to use vacuum rotary evaporator.
- 7. the method for the synthesis 2H- aziridine acid amides as described in any one of claim 1 to 6, it is characterised in that described pure Change using column chromatography, solvent is dichloromethane/ethyl acetate=4：1.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108689901A (en) * | 2018-05-05 | 2018-10-23 | 西北大学 | A kind of synthetic method of aziridine class compound |
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2017
- 2017-10-27 CN CN201711024172.2A patent/CN107628979B/en active Active
Non-Patent Citations (1)
| Title |
|---|
| EDWIN F.ULLMAN，ET AL.: "Photochemical Transposition of Ring Atoms in Five-Membered Heterocycles. The Photorearrangement of 3,5-Diphenylisoxazole", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108689901A (en) * | 2018-05-05 | 2018-10-23 | 西北大学 | A kind of synthetic method of aziridine class compound |
| CN108689901B (en) * | 2018-05-05 | 2020-04-28 | 西北大学 | Synthetic method of aziridine compound |
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| CN107628979B (en) | 2020-04-14 |
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