CN107365278A - A kind of polysubstituted isoxazole alkane derivatives and preparation method thereof - Google Patents
A kind of polysubstituted isoxazole alkane derivatives and preparation method thereof Download PDFInfo
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- CN107365278A CN107365278A CN201710433304.0A CN201710433304A CN107365278A CN 107365278 A CN107365278 A CN 107365278A CN 201710433304 A CN201710433304 A CN 201710433304A CN 107365278 A CN107365278 A CN 107365278A
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- 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
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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
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Abstract
The present invention relates to a kind of polysubstituted isoxazole alkane derivatives and preparation method thereof, its structural formula such as formula (I) are shown：Formula (I), wherein, R1、R2For substituted aromatic base or alkyl, the substituent on Ar can be alkoxy, halogen or alkyl；The substituted aromatic base is phenyl or naphthyl, and alkyl generally includes：Methyl, ethyl, cyclohexyl, preparation method step are as follows：At room temperature, under air or nitrogen atmosphere, by the nitrone derivative shown in formula (II), photochemical catalyst dissolving shown in the compound containing alkene structures and formula (IV) shown in formula (III) is in organic solvent, it is well mixed, it is placed under blue led s lamps or incandescent lamp after illumination a few hours question response is complete, rotates solvent, again through silica gel column chromatography separating purification, you can obtain polysubstituted isoxazole alkane derivatives；This method solve existing isoxazole alkane derivatives synthesis needs high-temperature heating system, and power consumption is high, and requirement of the condition harshness to equipment is big, and mild condition, method are simple and easy to operate, yield is high.
Description
Technical field
The present invention relates to a kind of polysubstituted isoxazole alkane derivatives and preparation method thereof, belong to technical field of organic synthesis.
Background technology
Isoxazole alkane skeleton is widely existed among natural products and drug molecule with bioactivity, due to
Its unique nitrogen oxa- ring structure, therefore it or the important raw material midbody of many chemical industry products and other natural products,
Such as the chemical bond between nitrogen oxygen therein is cut off by reduction process, it is possible to obtain gamma-amino alcohol.According to document report
Road, pass through a series of conversion reaction, it is possible to all kinds of important chemical raw material intermediates are obtained, such as benzazolyl compounds 1, benzene
And tetrahydrofuran-compound 2, benzopyran compounds 3.
At present, polysubstituted isoxazole alkane derivatives report and few is synthesized, and existing synthetic method uses high temperature mostly
Heating systems, power consumption is high, and requirement of the condition harshness to equipment is big, and low yield.Therefore, seek to a kind of mild condition, side
The synthetic method for the isoxazole alkane derivatives that method is simple and easy to operate yield is high is current urgent problem to be solved.
The content of the invention
It is an object of the invention to solve the deficiencies in the prior art, there is provided a kind of polysubstituted isoxazole alkane derivatives.
Second object of the present invention is to provide a kind of method for preparing isoxazole alkane derivatives.
The technical solution adopted for the present invention to solve the technical problems is：
A kind of isoxazole alkane derivatives, shown in its structural formula such as formula (I)：
Wherein, R1、R2For substituted aromatic base or alkyl, the substituent on Ar can be alkoxy, halogen or alkyl；Institute
It is phenyl or naphthyl to state substituted aromatic base, and alkyl generally includes：Methyl, ethyl, cyclohexyl etc..
Preferably, the substituted aromatic base is phenyl.
A kind of method for preparing isoxazole alkane derivatives, comprises the following steps：
At room temperature, under air or nitrogen atmosphere (more preferable under nitrogen atmosphere), the nitrone shown in formula (III) is derived
Thing, the photochemical catalyst dissolving shown in the compound containing alkene structures and formula (IV) shown in formula (III) mix in organic solvent
Close uniform, be placed under blue led s lamps (or other visible light sources such as incandescent lamp) after illumination a few hours question response is complete, revolving
Solvent, then through silica gel column chromatography separating purification, you can obtain polysubstituted isoxazole alkane derivatives；
Wherein, the substituent on formula (II) Ar is halogen, alkoxy or alkyl.
The reaction scheme is：
Preferably, the compound containing alkene structures is Beta-methyl styrene compound or cyclopentene or 2- first
Base 2- butylene.
Preferably, the nitrone derivative, the molar ratio of compound and photochemical catalyst containing alkene structures are
1:2:0.025。
Preferably, the organic solvent is selected from dichloromethane, dichloroethanes, acetonitrile or tetrahydrofuran.
Preferably, the volume that feeds intake of the organic solvent is 10-20mL/mmol nitrones.
(or other visible light sources such as incandescent lamp) irradiation reaction time is 12- preferably, the blue led s lamps
20h。
Preferably, the silica gel column chromatography separating purification solvent for use is the mixed solvent of petroleum ether and ethyl acetate.
It is further preferred that the volume ratio of the petroleum ether and ethyl acetate is 50-20:1.
Beneficial effects of the present invention are：
1st, the invention provides a kind of Multi substituted benzenes isoxazole alkane derivatives, the derivative to have huge potential application
Value.According to existing document and patent report, Multi substituted benzenes isoxazole alkane derivatives have various path for transformation, Ke Yizuo
For the intermediate of many industrial chemicals, so compound provided by the invention has higher researching value, medicine may be used as
The research and development such as exploitation and the synthesis of industrial chemicals intermediate use.The present invention, which can also be used as, to be synthesized other and contains isoxazole alkane and spread out
The raw material of biology uses.
2nd, the invention provides a kind of method of the polysubstituted isoxazole alkane derivatives of succinct one-step synthesis method, this method
Solving existing isoxazole alkane derivatives synthesis needs high-temperature heating system, and power consumption is high, and requirement of the condition harshness to equipment is big,
And the problem of low yield, in mild condition, method it is simple and the advantages that easy to operate yield is high.
Embodiment
In order that technical scheme and advantage are more clearly understood, the present invention is carried out with reference to embodiments
It is further described.It should be appreciated that specific embodiment described herein is not used to limit only to explain the present invention
The present invention.
Embodiment 1
Into 7mL round-bottomed flasks, 59mg (0.3mmol) diphenyl nitrone, 53mg (0.45mmol) Beta-methyl benzene second are added
Alkene, 1.2mg (0.0075mmol) photochemical catalysts and 4mL dichloromethane, nitrogen is led to after stirring and is placed in blueness after 30 minutes
Under LEDs lamps, illumination reaction 12h at room temperature.After reaction terminates, after the rotated evaporimeter concentration of reaction dissolvent is spin-dried for, then with
Volume ratio is 50:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography purifies and separates, obtained as eluant, eluent
To corresponding polysubstituted isoxazole alkane derivatives, its reaction equation is：
Product purity is 99%, yield 85%.Nuclear magnetic data is analyzed：1H NMR (400MHz, CDCl3)：δH7.31-
7.25 (m, 2H), 7.18-7.16 (m, 5H), 7.11-7.06 (m, 5H), 6.97 (t, J=7.3Hz, 1H), 6.83-6.82 (m,
2H), 4.94 (d, J=8.8Hz, 1H), 4.67 (dq, J=9.4,6.0 Hz, 1H), 3.63 (t, J=9.0Hz, 1H), 1.42 (d,
J=6.0Hz, 3H)
13C NMR(100MHz,CDCl3):δC 151.7,138.9,135.9,129.4,128.8,128.1, 128.0,
127.9,127.2,127.0,121.5,115.2,77.8,74.8,60.3,17.7.
Embodiment 2
Into 7mL round-bottomed flasks, addition 59mg (0.3mmol) diphenyl nitrone, 47mg (0.45mmol) styrene,
1.2mg (0.0075mmol) photochemical catalysts and 4mL dichloromethane, nitrogen is led to after stirring and is placed in blue led s after 30 minutes
Under lamp, illumination reaction 17h at room temperature.After reaction terminates, after the rotated evaporimeter concentration of reaction dissolvent is spin-dried for, then with volume
Than for 30:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography purifies and separates, obtains phase as eluant, eluent
The polysubstituted isoxazole alkane derivatives answered, its reaction equation are：
Product purity is 99%, yield 52%.Its nuclear magnetic data is analyzed：1H NMR(400MHz, CDCl3):δH
7.29-7.24 (m, 3H), 7.16-7.10 (m, 5H), 6.95-6.92 (m, 2H), 4.99 (d, J=7.9Hz, 1H), 4.50 (t, J
=7.6Hz, 1H), 4.33-4.29 (m, 1H), 4.07 (dd, J=14.2,7.1Hz, 1H)
13C NMR(100MHz,CDCl3):δC 152.2,138.4,137.1,129.1,129.0,128.0, 128.0,
127.9,127.1,126.9,121.9,115.0,74.9,71.9,54.1.
Embodiment 3
Into 7mL round-bottomed flasks, 59mg (0.3mmol) diphenyl nitrone, 53mg (0.45mmol) indenes, 1.2mg are added
(0.0075mmol) photochemical catalyst and 6mL dichloromethane, nitrogen is led to after stirring and is placed in after 30 minutes under blue led s lamps,
Illumination reaction 12h at room temperature.After reaction terminates, after the concentration of reaction dissolvent rotated evaporimeter is spin-dried for, then using volume ratio as
40:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography purifies and separates, obtained corresponding as eluant, eluent
Polysubstituted isoxazole alkane derivatives, its reaction equation are：
Product purity is 99%, yield 81%.Its nuclear magnetic data is analyzed：1H NMR(400MHz, CDCl3):δH
7.23-7.16 (m, 9H), 7.06 (t, J=8.2Hz, 3H), 6.93 (t, J=7.3Hz, 1H), 6.76 (t, J=7.5Hz, 1H),
6.03 (d, J=7.7Hz, 1H), 5.22 (td, J=6.4,2.1Hz, 1H), 5.01 (d, J=8.7Hz, 1H), 4.44-4.40
(m, 1H), 3.38 (d, J=16.7Hz, 1H), 3.25 (dd, J=17.4,6.4Hz, 1H)
13C NMR(100MHz,CDCl3):δC 151.2,142.1,139.9,138.8,128.8,128.2, 128.2,
127.5,127.3,126.7,125.9,124.6,122.1,115.8,82.6,74.3,60.5,37.7.
Embodiment 4
Into 7mL round-bottomed flasks, 59mg (0.3mmol) diphenyl nitrone, 67mg (0.45mmol) are added) Beta-methyl -4-
Methoxy styrene, 1.2mg (0.0075mmol) photochemical catalysts and 4mL dichloromethane, nitrogen is led to after stirring after 30 minutes
It is placed under blue led s lamps, at room temperature illumination reaction 12h.After reaction terminates, the rotated evaporimeter concentration of reaction dissolvent is spin-dried for
Afterwards, then using volume ratio as 50:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography purifying as eluant, eluent
Separation, obtains corresponding polysubstituted isoxazole alkane derivatives, and its reaction equation is：
Product purity is 99%, yield 81%.Its nuclear magnetic data is analyzed：1H NMR(400MHz, CDCl3):δH
7.36-7.25 (m, 4H), 7.18 (s, 3H), 7.07-6.85 (m, 4H), 6.72-6.63 (m, 3 H), 4.90 (d, J=8.7Hz,
1H), 4.58 (dq, J=9.6,6.0Hz, 1H), 3.74 (s, 3H), 3.57 (t, J=9.1Hz, 1H), 1.40 (d, J=6.0Hz,
3H).
13C NMR(100MHz,CDCl3):δC 158.4,151.6,138.9,130.2,128.6,127.9, 127.7,
127.7,127.0,121.2,115.0(s),113.3,77.8,74.6,59.4,55.1,17.5.
Embodiment 5
Into 7mL round-bottomed flasks, 59mg (0.3mmol) diphenyl nitrone, 61mg (0.45mmol) are added) Beta-methyl -2-
Fluorobenzene ethene, 1.2mg (0.0075mmol) photochemical catalysts and 4mL dichloromethane, nitrogen is led to after stirring and is placed in after 30 minutes
Under blue led s lamps, illumination reaction 14h at room temperature.After reaction terminates, after the rotated evaporimeter concentration of reaction dissolvent is spin-dried for,
Again using volume ratio as 50:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography purifying point as eluant, eluent
From obtaining polysubstituted isoxazole alkane derivatives, its reaction equation accordingly is：
Product purity is 99%, yield 60%.Its nuclear magnetic data is analyzed：1H NMR(400MHz, CDCl3):δH
7.37-7.35(m,1H),7.24-7.19(m,4H),7.10-7.08(m,3H),7.02-7.00 (m,3H),6.94-6.90(m,
1H), 6.88-6.82 (m, 1H), 6.80-6.77 (m, 1H), 4.98 (d, J=9.1Hz, 1H), 4.78-4.71 (m, 1H), 3.99
(t, J=9.1Hz, 1H), 1.42 (d, J=6.0Hz, 3H)
13C NMR(100MHz,CDCl3):δC161.1 (d, J=244.8Hz), 151.4,139.0,129.1 (d, J=
4.2Hz), 128.8,128.1,127.6,127.3,123.8 (d, J=11.3Hz), 123.8 (d, J=3.2Hz), 121.5,
(115.1,114.9 d, J=22.7Hz), 76.4,73.3,52.0,17.7.
Embodiment 6
Into 7mL round-bottomed flasks, 59mg (0.3mmol) diphenyl nitrone, 67mg (0.45mmol) are added) Beta-methyl -3-
Methoxy styrene, 1.2mg (0.0075mmol) photochemical catalysts and 4mL dichloromethane, nitrogen is led to after stirring after 30 minutes
It is placed under blue led s lamps, at room temperature illumination reaction 12h.After reaction terminates, the rotated evaporimeter concentration of reaction dissolvent is spin-dried for
Afterwards, then using volume ratio as 50:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography purifying as eluant, eluent
Separation, obtains corresponding polysubstituted isoxazole alkane derivatives, and its reaction equation is：
Product purity is 99%, yield 82%.Its nuclear magnetic data is analyzed：1H NMR(400MHz, CDCl3):δH
7.22-7.20 (m, 2H), 7.15-7.13 (m, 5H), 7.03 (d, J=7.9Hz, 2H), 6.98 (t, J=7.9Hz, 1H), 6.92
(t, J=7.3Hz, 1H), 6.62 (dd, J=8.2,2.3Hz, 1H), 6.42 (d, J=7.6Hz, 1H), 6.24 (s, 1H), 4.89
(d, J=8.8Hz, 1H), 4.59 (dq, J=9.6,6.0 Hz, 1H), 3.57-3.53 (m, 4H), 1.37 (d, J=6.0Hz,
3H).
13C NMR(100MHz,CDCl3):δC 159.2,151.6,138.9,137.3,129.0,128.7, 128.0,
127.9,127.2,122.0,121.4,115.1,114.5,113.0,77.8,74.7,60.1,55.1, 17.6.
Embodiment 7
Into 7mL round-bottomed flasks, 74mg (0.3mmol) N- phenyl-alpha-naphthyl nitrones, 53mg (0.45mmol) are added) β-
Methyl styrene, 1.2mg (0.0075mmol) photochemical catalysts and 5mL dichloromethane, it is rearmounted that nitrogen 30 minutes is led to after stirring
Under blue led s lamps, illumination reaction 12h at room temperature.After reaction terminates, the rotated evaporimeter concentration of reaction dissolvent is spin-dried for
Afterwards, then using volume ratio as 45:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography purifying as eluant, eluent
Separation, obtains corresponding polysubstituted isoxazole alkane derivatives, and its reaction equation is：
Product purity is 99%, yield 70%.Its nuclear magnetic data is analyzed：1H NMR(400MHz, CDCl3):δH
7.98 (d, J=7.2Hz, 1H), 7.79-7.67 (m, 3H), 7.43-7.32 (m, 3H), 7.24 (t, J=7.9Hz, 2H), 7.05
(d, J=7.9Hz, 2H), 6.96 (t, J=7.3Hz, 1H), 6.85-6.80 (m, 5H), 5.71 (d, J=9.1Hz, 1H), 4.72
(dq, J=12.2,6.1Hz, 1H), 3.89 (t, J=8.7Hz, 1H), 1.45 (d, J=6.1Hz, 3H)
13C NMR(100MHz,CDCl3):δC 151.4,136.4,134.4,133.4,130.6,129.2, 128.8,
128.6,127.8,127.4,126.8,126.0,125.5,125.2,123.3,121.6,115.6,79.6, 70.3,60.8,
18.0.
Embodiment 8
Into 7mL round-bottomed flasks, 61mg (0.3mmol) N- phenyl-α-cyclohexyl nitrone, 53mg (0.45mmol) are added)
Beta-methyl styrene, 1.2mg (0.0075mmol) photochemical catalysts and 4mL dichloromethane, nitrogen is led to after stirring after 30 minutes
It is placed under blue led s lamps, at room temperature illumination reaction 19h.After reaction terminates, the rotated evaporimeter concentration of reaction dissolvent is spin-dried for
Afterwards, then using volume ratio as 50:1 petroleum ether：The mixed solution of ethyl acetate carries out silica gel column chromatography purifying as eluant, eluent
Separation, obtains corresponding polysubstituted isoxazole alkane derivatives, and its reaction equation is：
Product purity is 99%, yield 55%.Its nuclear magnetic data is analyzed：1H NMR(400MHz, CDCl3):δH
7.35 (t, J=7.8Hz, 2H), 7.25-7.17 (m, 3H), 7.11 (d, J=8.4Hz, 2H), 7.00-6.97 (m, 3H), 4.07
(dq, J=11.7,5.9Hz, 1H), 3.68 (dd, J=7.5,5.7Hz, 1H), 3.15 (dd, J=9.5,5.5Hz, 1H), 2.09
(d, J=11.9Hz, 1H), 1.87-1.67 (m, 5H), 1.35-1.30 (m, 4H), 1.23-1.13 (m, 2H), 1.01 (qd, J=
12.4,3.2Hz,1H).
13C NMR(100MHz,CDCl3):δC 152.81(s),140.5,129.3,128.9,128.2, 126.9,
120.8,113.7,83.4,81.4,63.8,44.4,31.0,30.4,26.6,26.4,26.3,16.2.
Embodiment 9
Into 7mL round-bottomed flasks, 65mg (0.3mmol) N- phenyl-α -2- fluorophenyl nitrones, 53mg are added
(0.45mmol)) Beta-methyl styrene, 1.2mg (0.0075mmol) photochemical catalysts and 4mL dichloromethane, lead to after stirring
Nitrogen is placed in after 30 minutes under blue led s lamps, at room temperature illumination reaction 12h.After reaction terminates, the rotated steaming of reaction dissolvent
After hair instrument concentration is spin-dried for, then using volume ratio as 50:1 petroleum ether：The mixed solution of ethyl acetate carries out silicon as eluant, eluent
Gel column chromatography eluting separation, obtains corresponding polysubstituted isoxazole alkane derivatives, and its reaction equation is：
Product purity is 99%, yield 87%.Its nuclear magnetic data is analyzed：1H NMR(400MHz, CDCl3):δH
7.71 (t, J=7.3Hz, 1H), 7.32-7.28 (m, 2H), 7.15-7.07 (m, 7H), 7.02-6.95 (m, 3H), 6.78-
6.73 (m, 1H), 5.30 (d, J=8.8Hz, 1H), 4.67 (dq, J=12.2,6.1Hz, 1H), 3.76 (t, J=8.6Hz,
1H), 1.43 (d, J=6.1Hz, 3H)
13C NMR(100MHz,CDCl3):δC159.5 (d, J=245.8Hz), 151.4,136.1,129.4 (d, J=
3.8Hz), 129.2,128.9 (d, J=8.4Hz), 128.8,127.9,127.1,126.5 (d, J=13.0 Hz), 124.1 (d,
), J=3.2Hz 121.8,115.3,114.7 (d, J=21.6Hz), 78.9,68.0,59.9,18.1.
Embodiment described above is a kind of preferable scheme of the present invention, not the present invention is made any formal
Limitation, on the premise of without departing from the technical scheme described in claim also have other variants and remodeling.
Claims (10)
1. a kind of isoxazole alkane derivatives, it is characterised in that shown in its structural formula such as formula (I)：
Wherein, R1、R2For substituted aromatic base or alkyl, the substituent on Ar is alkoxy, halogen or alkyl；The substitution virtue
Perfume base is phenyl or naphthyl, and alkyl includes：Methyl, ethyl and cyclohexyl.
2. a kind of isoxazole alkane derivatives according to claim 1, it is characterised in that the substituted aromatic base is phenyl.
3. a kind of a kind of preparation method of isoxazole alkane derivatives of claim 1 or 2, it is characterised in that including following step
Suddenly：
At room temperature, under air or nitrogen atmosphere, by the nitrone derivative shown in formula (III), alkene is contained shown in formula (III)
Photochemical catalyst dissolving shown in the compound and formula (IV) of hydrocarbon structure is well mixed in organic solvent, is placed in blue led s lamps
Or under incandescent lamp after illumination a few hours question response is complete, solvent is rotated, then through silica gel column chromatography separating purification, you can obtain more
Substitute isoxazole alkane derivatives；
Wherein, the substituent on formula (III) Ar is halogen, alkoxy or alkyl.
4. a kind of preparation method of isoxazole alkane derivatives according to claim 3, it is characterised in that described to contain alkene knot
The compound of structure is Beta-methyl styrene compound or cyclopentene or 2- methyl 2- butylene.
5. a kind of preparation method of isoxazole alkane derivatives according to claim 3, it is characterised in that the nitrone derives
Thing, the molar ratio of compound and photochemical catalyst containing alkene structures is 1:2:0.025.
A kind of 6. preparation method of isoxazole alkane derivatives according to claim 3, it is characterised in that the organic solvent choosing
From dichloromethane, dichloroethanes, acetonitrile or tetrahydrofuran.
7. a kind of preparation method of isoxazole alkane derivatives according to claim 3, it is characterised in that the organic solvent
The volume that feeds intake is 10-20mL/mmol nitrones.
A kind of 8. preparation method of isoxazole alkane derivatives according to claim 3, it is characterised in that the blue led s lamps
Or the incandescent lamp irradiation reaction time is 12-20h.
A kind of 9. preparation method of isoxazole alkane derivatives according to claim 3, it is characterised in that the silica gel column chromatography
Solvent for use is isolated and purified as petroleum ether and the mixed solvent of ethyl acetate.
A kind of 10. preparation method of isoxazole alkane derivatives according to claim 3, it is characterised in that the petroleum ether with
The volume ratio of ethyl acetate is 50-20:1.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107746392A (en) * | 2017-12-05 | 2018-03-02 | 河南师范大学 | A kind of preparation method of the oxazole alkyl compound containing caged scaffold |
| CN109796422A (en) * | 2019-03-24 | 2019-05-24 | 盐城锦明药业有限公司 | A kind of light-catalyzed reaction is preparing the application in oxazolidine structural compounds |
| CN112939883A (en) * | 2019-11-26 | 2021-06-11 | 兰州大学 | Preparation method of polysubstituted 1, 3 oxazolidine compound |
-
2017
- 2017-06-09 CN CN201710433304.0A patent/CN107365278A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| JOYANN S.BARBER等: "Nitrone Cycloaddition of 1,2-Cyclohexadiene", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
| LEI XIE等: "Cu(II)-catalyzed enantioselective 1,3-dipolar cycloaddition of nitrones with α,β-unsaturated acyl phosphonates", 《TETRAHEDRON》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107746392A (en) * | 2017-12-05 | 2018-03-02 | 河南师范大学 | A kind of preparation method of the oxazole alkyl compound containing caged scaffold |
| CN107746392B (en) * | 2017-12-05 | 2020-10-09 | 河南师范大学 | Preparation method of oxazolidine compound containing bridged ring structure |
| CN109796422A (en) * | 2019-03-24 | 2019-05-24 | 盐城锦明药业有限公司 | A kind of light-catalyzed reaction is preparing the application in oxazolidine structural compounds |
| CN109796422B (en) * | 2019-03-24 | 2023-04-11 | 盐城师范学院 | Application of photocatalytic reaction in preparation of oxazolidine structural compound |
| CN112939883A (en) * | 2019-11-26 | 2021-06-11 | 兰州大学 | Preparation method of polysubstituted 1, 3 oxazolidine compound |
| CN112939883B (en) * | 2019-11-26 | 2024-01-16 | 兰州大学 | Preparation method of polysubstituted 1, 3-oxazolidine compound |
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