CN110194735A - A kind of chirality 3-(2- pyridine) -3- aryl substitutional amine-group compound visible light asymmetry catalysis synthetic method - Google Patents
A kind of chirality 3-(2- pyridine) -3- aryl substitutional amine-group compound visible light asymmetry catalysis synthetic method Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
Abstract
A kind of chirality 3-(2- pyridine) -3- aryl substitutional amine-group compound visible light asymmetry catalysis synthetic method, synthetic route is as follows:Wherein, the structure of chiral spiro phosphonic acids and DPZ are as follows:Under an argon atmosphere,NAryl replaces glycine (I) and alpha-aromatic-α-(2- pyridine) to replace terminal olefin (II) in THF or toluene using DPZ, lithium hexafluoro phosphate and chiral spiro phosphonic acids as catalyst, under visible light illumination in -35 DEG C ~ -40 DEG C fully reactings, it is obtained target chiral amine compounds (III) through column chromatographic isolation and purification, compound I, compound II, R in compound III1=CN, H, F, Cl, Br, Ph or Me, R2=H, Me, Cl or Br, R3=H, F, Cl, Br, Me or MeO.Formula III compound represented is chirality 3-(2- pyridine) -3- aryl substitutional amine-group compound.
Description
Technical field
The invention belongs to pharmaceutical intermediates to synthesize field, and in particular to a kind of chirality 3- (2- pyridine) -3- aryl substitution amine
The visible light asymmetry catalysis synthetic method of class compound.
Background technique
Chiral 3- (2- pyridine) -3- aryl substitutional amine-group compound is in fields such as synthetic drug, natural products, functional materials
It has a wide range of applications.In environment-friendly organic synthesis chemical research, develop it is a kind of it is environmentally protective, efficiently synthesize chiral 3- (2- pyrrole
Pyridine) method of -3- aryl substitutional amine-group compound is of great significance.Reported synthesis of chiral 3- (2- pyridine) -3- aryl
The method of substitutional amine-group compound only has the transition metal-catalyzed asymmetry of 3- aryl -3- (2- pyridine)-substituted allyl amine and adds
Hydrogen reacts (Botteghi, C.；Del Ponte,G.；Marchetti,C.J.Mol.Catal.1993,83,L1；Marchetti,
M.；Alberico,E.；Bertucci,C.；Botteghi,C.；Del Ponte,G.J.Mol.Catal A:
Chemical1997,125,109.).The catalyst system generally 50% or so and is being produced since C-N key hydrogenolysis yield can occur
Object optical voidness is 60% hereinafter, the three-dimensional choosing of the height for being therefore not used to chiral 3- (2- pyridine) -3- aryl substitutional amine-group compound
Selecting property is synthesized with high yield.
In recent years, it is seen that light-catalyzed reaction is widely applied because of its green, efficiently, mildly in organic synthesis field.
Since reaction condition heavy metal free remains, product replaces glycine without doing heavy metals removal, by visible light catalytic N- aryl
Replace conjugate addition-protonation reaction of terminal olefin also therefore with very big before with alpha-aromatic-α-(2- pyridine)
Scape.
Summary of the invention
The purpose of the present invention is to provide a kind of visible lights of chirality 3- (2- pyridine) -3- aryl substitutional amine-group compound not
Asymmetric catalytic synthetic method.
A kind of visible light asymmetry catalysis synthetic method of chirality 3- (2- pyridine) -3- aryl substitutional amine-group compound is closed
It is as follows at route:
Wherein, the structure of chiral spiro phosphonic acids and DPZ are as follows:
Synthesis process are as follows: under an argon atmosphere, N- aryl replaces glycine (I) and alpha-aromatic-α-(2- pyridine) to replace end alkene
Hydrocarbon (II) in THF or toluene using DPZ, lithium hexafluoro phosphate and chiral spiro phosphonic acids as catalyst, under visible light illumination in-
35 DEG C~-40 DEG C fully reactings obtain target chiral amine compounds (III), compound I, compound through column chromatographic isolation and purification
R in II, compound III1=CN, H, F, Cl, Br, Ph or Me, R2=H, Me, Cl or Br, R3=H, F, Cl, Br, Me or MeO.Formula
Tetrahydro chinolines chirality 3- (2- pyridine) -3- aryl substitutional amine-group compound shown in III.This product has important application
Value.As that wherein will replace amine progress two steps chemical reaction that optical voidness R- configuration benzene pyrrole can be obtained by 3- (2- pyridine) -3- phenyl
Propylamine antiallergic (pheniramine).The protective atmosphere is nitrogen or argon gas.
Preferably, compound I, compound II, R in compound III1=H, F, Cl or Me, R2=H or Br, R3=H or
MeO。
Further, the molar ratio of the compound I, compound II, DPZ, chiral spiro phosphonic acids and lithium hexafluoro phosphate is
1 ︰ (1~1.5) ︰ (0.002~0.003) ︰ (0.1~0.15) ︰ (0.3~0.5).
It further, need to be by the reaction flask for installing each reaction raw materials by least taking out three times when being reacted under argon atmosphere
It after vacuum, freezes (- 70~-80 DEG C of 3~5min of holding), then restore to room temperature, is filled with argon gas protection.
Further, the visible light by power is 3W, wavelength provides for the blue LED lamp of 450-455nm, the blue lamp
The distance between reactant is 5~10cm.
Further, eluant, eluent by n-hexane and ethyl acetate volume ratio is 80~5:1 when the column chromatographic isolation and purification
Composition.
Compared to the prior art, the method for the present invention the utility model has the advantages that
The present invention uses the DPZ photochemical catalyst of no metal in the reaction, and catalyst amount is few, high catalytic efficiency, and reacts item
Part is mild, stability and high efficiency, easy to operate, environmental-friendly, and product yield is high, good, environmentally protective, the great popularization and application of selectivity
Value.
Specific embodiment
Technical solution of the present invention is further discussed in detail with reference to embodiments, but protection scope of the present invention
It is not limited thereto.
In following embodiments, organic photochemical catalyst DPZ can refer to document (Yu Zhao,Chenhao Zhang,Kek
Foo Chin,Oldˇrich Pytela,Guo Wei,Hongjun Liu,Filip Bures*and Zhiyong Jiang*
RSC Adv., 2014,4,30062) it prepares.Chiral spiro phosphonic acids CPA is bought from Daicel drug chiral technology (Shanghai)
Co., Ltd, lithium hexafluoro phosphate are bought from Bellingwell company.
Embodiment 1
A kind of visible light asymmetry catalysis synthetic method of chirality 3- (2- pyridine) -3- substitutional amine-group compound, reaction equation is such as
Shown in lower.(R) specific preparation process is as follows for aniline by-N- (3- phenyl -3- (2- pyridyl group) propyl):
Wherein, the structure of chiral spiro phosphonic acids and DPZ are as follows:
1 milligram of DPZ of organic photochemical catalyst is dissolved in 200 μ L toluene, 14.2 microlitres (0.0002mmol, 0.002 equivalent) is extracted
Into 25 milliliters of Schlenk pipes (Schlenk tube), toluene is dried up with air pump.N-phenylglycine is then added (to change
Close object I) 15.1 milligrams of (0.1mmol), 2- (1- benzene alkenyl) 21.7 milligrams of pyridines (i.e. compound II) (0.12mmol), chiral spiral shell
9 milligrams of ring phosphonic acids (0.015mmol), 6 milligrams of lithium hexafluoro phosphate (0.04mmol), four after 4 milliliters of purifying dryings are then added
Schlenk pipe is freezed (- 80 DEG C of holding 3min) after vacuumizing three times, then restored to room temperature by hydrogen furans, is filled with argon gas guarantor
Shield, Schlenk pipe is placed in -35 DEG C of insulating boxs, in a 3W blue LED lamp (wavelength 450-455nm, Schlenk pipe distance
LED light 5cm) it stirs 60 hours under irradiation condition, reaction terminates, and boils off tetrahydrofuran with Rotary Evaporators, directly passes through column layer
Analysis separation (80~5:1 of n-hexane/ethyl acetate volume ratio) obtains 25.1 milligrams of yellow solid compound III, and yield is
87%, optical voidness 94%ee.Its fusing point is 67.2-68.9 DEG C, nuclear magnetic data are as follows:1HNMR(300MHz,CDCl3)δ8.59(d,
J=4.3Hz, 1H), 7.57 (td, J=7.7,1.6Hz, 1H), 7.44-7.28 (m, 4H), 7.25-7.07 (m, 5H), 6.67 (t,
J=7.3Hz, 1H), 6.53 (d, J=7.9Hz, 2H), 4.24 (t, J=7.7Hz, 1H), 3.74 (s, 1H), 3.11 (t, J=
7.0Hz, 2H), 2.61 (dq, J=14.4,7.1Hz, 1H), 2.40 (dq, J=14.3,7.2Hz, 1H))；13C NMR(75MHz,
CDCl3)δ163.3,149.2,148.3,143.3,136.5,129.1,128.6,128.0,126.6,122.9,121.4,
117.1,112.7,51.3,42.3,34.6；High-resolution data are as follows: 311.1534 (M+Na of HRMS (ESI) m/z+),calc.for
C20H20N2Na 311.1524.
Embodiment 2
The reaction equation for synthesizing (R)-N- (3- phenyl -3- (2- pyridyl group) propyl) -4- aminoanisole is as follows.
In the present embodiment, N- (to the methoxyl group-phenyl) glycine of the N-phenylglycine in embodiment 1 is replaced,
Its step is same as Example 1, obtains (R)-N- (3- (4- methoxyl group-phenyl) -3- (2- pyridyl group) propyl) aniline 26.4mg,
For yellow oil, yield 83%, optical voidness 94%ee.Nuclear magnetic data are as follows:1H NMR(300MHz,CDCl3)δ8.58(d,J
=4.2Hz, 1H), 7.56 (td, J=7.7,1.6Hz, 1H), 7.41-7.27 (m, 4H), 7.24-7.06 (m, 3H), 6.74 (d, J
=8.8Hz, 2H), 6.50 (d, J=8.9Hz, 2H), 4.22 (t, J=7.7Hz, 1H), 3.73 (s, 3H), 3.05 (t, J=
7.0Hz, 2H), 2.57 (dq, J=14.5,7.1Hz, 1H), 2.38 (td, J=14.3,7.3Hz, 1H)；13C NMR(75MHz,
CDCl3)δ163.2,151.8,149.1,143.2,142.4,136.5,128.5,127.9,126.5,122.8,121.4,
114.7,114.0,55.7,51.1,43.2,34.6；High-resolution data are as follows: 341.1635 (M+Na of HRMS (ESI) m/z+),
calc.for C21H22N2ONa 341.1630.
Embodiment 3
The reaction equation for synthesizing (R)-N- (3- (4- fluoro-phenyl) -3- (2- pyridyl group) propyl)-aniline is as follows.
In the present embodiment, 2- (1- (4- fluorobenzene) alkenyl) pyridine of 2- (the 1- benzene alkenyl) pyridine in embodiment 1 is replaced,
Other steps are same as Example 1, obtain (R)-N- (3- (4- fluoro-phenyl) -3- (2- pyridyl group) propyl)-aniline 27.6mg,
For yellow oil, yield 90%, optical voidness 92%ee.Nuclear magnetic data are as follows:1H NMR(300MHz,CDCl3)δ8.59(d,J
=4.4Hz, 1H), 7.58 (td, J=7.8,1.5Hz, 1H), 7.37-7.28 (m, 2H), 7.22-7.06 (m, 4H), 6.99 (t, J
=8.7Hz, 2H), 6.68 (t, J=7.3Hz, 1H), 6.53 (d, J=7.8Hz, 2H), 4.22 (t, J=7.7Hz, 1H), 3.61-
3.01 (m, 3H), 2.58 (dq, J=14.3,7.1Hz, 1H), 2.36 (dq, J=14.3,7.2Hz, 1H)；13C NMR(75MHz,
CDCl3)δ162.9,161.6(d,JF–C=244.9Hz), 149.2,148.1,138.9 (d, JF–C=3.1Hz), 136.7,
129.4(d,JF–C=7.8Hz), 129.2,122.9,121.6,117.2,115.4 (d, JF–C=21.2Hz), 112.7,50.3,
42.2,34.7；High-resolution data are as follows: 307.1613 (M+H of HRMS (ESI) m/z+),calc.for C20H20N2F 307.1611.
Embodiment 4
The reaction equation for synthesizing (R)-N- (3- (the chloro- phenyl of 4-) -3- (2- pyridyl group) propyl)-aniline is as follows.
In the present embodiment, 2- (1- (4- chlorobenzene) alkenyl) pyridine of 2- (the 1- benzene alkenyl) pyridine in embodiment 1 is replaced,
Other steps are same as Example 1, obtain (R)-N- (3- (the chloro- phenyl of 4-) -3- (2- pyridyl group) propyl)-aniline 26.7mg,
For yellow oil, yield 83%, optical voidness 92%ee.Nuclear magnetic data are as follows:1H NMR(300MHz,CDCl3)δ8.54(d,J
=4.0Hz, 1H), 7.53 (t, J=7.6Hz, 1H), 7.24-7.16 (d, J=6.4Hz, 4H), 7.13-6.96 (t, J=
7.3Hz, 4H), 6.63 (t, J=7.3Hz, 1H), 6.49 (d, J=7.9Hz, 2H), 4.16 (t, J=7.7Hz, 1H), 3.75 (s,
1H), 3.04 (t, J=6.9Hz, 2H), 2.52 (dq, J=14.3,7.1Hz, 1H), 2.30 (dq, J=14.1,7.0Hz, 1H)；13C NMR(75MHz,CDCl3)δ162.5,149.2,148.0,141.7,136.7,132.3,129.3,129.2,128.7,
122.9,121.7,117.3,112.7,50.4,42.1,34.5；High-resolution data are as follows: 323.1325 (M+H of HRMS (ESI) m/z+),calc.for C20H20N2Cl 323.1315.
Embodiment 5
The reaction equation for synthesizing (R)-N- (3- (3- fluoro-phenyl) -3- (2- pyridyl group) propyl)-aniline is as follows.
In the present embodiment, 2- (1- (3- fluorobenzene) alkenyl) pyridine of 2- (the 1- benzene alkenyl) pyridine in embodiment 1 is replaced,
Other steps are same as Example 1, obtain (R)-N- (3- (3- fluoro-phenyl) -3- (2- pyridyl group) propyl)-aniline 27.8mg,
For yellow oil, yield 91%, optical voidness 91%ee.Nuclear magnetic data are as follows:1H NMR(300MHz,CDCl3)δ8.57(d,J
=4.1Hz, 1H), 7.54 (td, J=7.7,1.6Hz, 1H), 7.21 (t, J=7.0Hz, 1H), 7.17-7.01 (m, 6H), 6.87
(td, J=8.4,1.8Hz, 1H), 6.65 (t, J=7.3Hz, 1H), 6.51 (d, J=7.8Hz, 2H), 4.20 (t, J=7.7Hz,
1H), 3.65 (s, 1H), 3.07 (t, J=7.0Hz, 2H), 2.55 (dq, J=14.6,7.1Hz, 1H), 2.33 (dq, J=14.1,
7.2Hz,1H)；13CNMR(75MHz,CDCl3)δ162.4,162.9(d,JF–C=245.9Hz), 149.3,148.1,145.9 (d,
JF–C=6.9Hz), 136.6,129.9 (d, JF–C=8.3Hz), 129.1,123.7 (d, JF–C=2.8Hz), 122.9,121.7,
117.2,114.8(d,JF–C=21.5Hz), 113.5 (d, JF–C=21.1Hz), 112.7,50.8,42.1,34.5；High-resolution number
According to are as follows: 307.1603 (M+H of HRMS (ESI) m/z+),calc.for C20H20N2F 307.1611.
Embodiment 6
The reaction equation for synthesizing (R)-N- (3- (4- methylphenyl) -3- (2- pyridyl group) propyl)-aniline is as follows.
In the present embodiment, 2- (the 1- benzene alkenyl) pyridine in embodiment 1 is replaced with 2- (1- (4- methylbenzene) alkenyl) pyridine
It changes, other steps are same as Example 1, obtain (R)-N- (3- (4- methylphenyl) -3- (2- pyridyl group) propyl)-aniline
26.9mg is yellow oil, yield 89%, optical voidness 92%ee.Nuclear magnetic data are as follows:1H NMR(300MHz,CDCl3)δ
8.61 (d, J=4.0Hz, 1H), 7.59 (t, J=7.1Hz, 1H), 7.40-7.27 (m, 2H), 7.23-7.03 (m, 6H), 6.70
(t, J=7.2Hz, 1H), 6.56 (d, J=7.8Hz, 2H), 4.23 (t, J=7.7Hz, 1H), 3.78 (s, 1H), 3.13 (t, J=
6.9Hz, 2H), 2.61 (td, J=14.0,6.9Hz, 1H), 2.50-2.27 (m, 4H)；13C NMR(75MHz,CDCl3)δ
163.5,149.1,148.2,140.2,136.5,136.2,129.3,129.1,127.8,122.8,121.4,117.0,
112.7,50.8,42.3,34.5,21.0；High-resolution data are as follows: 325.1681 (M+Na of HRMS (ESI) m/z+),calc.for
C21H22N2Na 325.1681.
Embodiment 7
The reaction equation for synthesizing (R)-N- (3- (2- methylphenyl) -3- (2- pyridyl group) propyl)-aniline is as follows.
In the present embodiment, 2- (the 1- benzene alkenyl) pyridine in embodiment 1 is replaced with 2- (1- (2- methylbenzene) alkenyl) pyridine
It changes, other steps are same as Example 1, obtain (R)-N- (3- (2- methylphenyl) -3- (2- pyridyl group) propyl)-aniline
25.4mg is yellow oil, yield 84%, optical voidness 94%ee.Nuclear magnetic data are as follows:1H NMR(300MHz,CDCl3)δ
8.68 (d, J=4.5Hz, 1H), 7.63 (td, J=7.7,1.5Hz, 1H), 7.49 (d, J=7.5Hz, 1H), 7.36-7.26 (m,
2H), 7.25-7.10 (m, 5H), 6.76 (t, J=7.3Hz, 1H), 6.64 (d, J=7.9Hz, 2H), 4.60 (t, J=7.5Hz,
1H), 3.92 (s, 1H), 3.25 (t, J=6.9Hz, 2H), 2.66 (dq, J=14.4,7.1Hz, 1H), 2.55-2.37 (m, 4H)
；13C NMR(75MHz,CDCl3)δ163.3,148.9,148.1,141.2,136.5,136.3,130.5,129.1,127.0,
126.4,126.2,122.9,121.3,117.1,112.7,46.6,42.3,34.6,20.0；High-resolution data are as follows: HRMS
(ESI)m/z 303.1864(M+H+),calc.for C21H23N2 303.1861.
Embodiment 8
The reaction equation for synthesizing (R)-N- (3- phenyl -3- (2- (4- bromine)-pyridyl group) propyl)-aniline is as follows.
In the present embodiment, 2- (the 1- benzene alkenyl) pyridine in embodiment 1 is replaced with 2- (1- benzene alkenyl)-(4- bromine)-pyridine
It changes, other steps are same as Example 1, obtain (R)-N- (3- phenyl -3- (2- (4- bromine)-pyridyl group) propyl)-aniline
26.8mg, be yellow solid, 96.3-97.9 DEG C of fusing point, yield 73%, optical voidness 91%ee.Nuclear magnetic data are as follows:1H NMR
(300MHz,CDCl3) δ 8.40 (d, J=5.2Hz, 1H), 7.43-7.27 (m, 6H), 7.26-.20 (m, 1H), 7.15 (t, J=
7.8Hz, 2H), 6.70 (t, J=7.3Hz, 1H), 6.56 (d, J=7.9Hz, 2H), 4.19 (t, J=7.6Hz, 1H), 3.11 (t,
J=7.0Hz, 2H), 2.58 (dq, J=14.3,7.1Hz, 1H), 2.38 (dq, J=14.2,7.2Hz, 1H)；13C NMR
(75MHz,CDCl3)δ164.7,149.9,147.7,142.4,133.2,129.2,128.8,127.9,126.9,126.3,
124.9,117.6,113.0,50.9,42.4,34.3；High-resolution data are as follows: 367.0811 (M+H of HRMS (ESI) m/z+),
calc.for C20H20BrN2 367.0810.
Compound prepared by embodiment 2 can obtain drug pheniramine (Fei Nila by reported method (2 step)
It is quick), the first step detailed process of following reaction can refer to Jorge M.M.Verkade, Lieke J.C.van Hemert,
Peter J.L.M.Quaedflieg,Paul L.Alsters,Floris L.van Delft and Floris
P.J.T.Rutjes.Mild and efficient deprotection of the amine protectingp-
Methoxyphenyl (PMP) group.Tetrahedron Letters, 2006,47:8109-8113. second step detailed process
It can refer to: Taki, Masayasu；Teramae,Shinichi；Nagatomo,Shigenori；Tachi,Yoshimitsu；
Kitagawa,Teizo；Itoh,Shinobu；Fukuzumi,Shunichi.Fine-Tuning of Copper(I)-
Dioxygen Reactivity by 2-(2-Pyridyl)ethylamine Bidentate Ligands.Journal of
the American Chemical Society 2002,124(22):6367-6377.
Claims (4)
1. a kind of chirality 3-(2- pyridine) the visible light asymmetry catalysis synthetic method of -3- aryl substitutional amine-group compound, it is special
Sign is that synthetic route is as follows:
Wherein, the structure of chiral spiro phosphonic acids and DPZ are as follows:
Under protective atmosphere,NAryl replaces glycine (I) and alpha-aromatic-α-(2- pyridine) that terminal olefin (II) is replaced to exist
Using DPZ, lithium hexafluoro phosphate and chiral spiro phosphonic acids as catalyst in THF or toluene, under visible light illumination in -35 DEG C ~ -40
DEG C fully reacting, obtains target chiral amine compounds (III), compound I, compound II, compound through column chromatographic isolation and purification
R in III1=CN, H, F, Cl, Br, Ph or Me, R2=H, Me, Cl or Br, R3=H, F, Cl, Br, Me or MeO.
2. chirality 3-(2- pyridine according to claim 1) the visible light asymmetry of -3- aryl substitutional amine-group compound urges
Be combined to method, which is characterized in that the compound I, compound II, DPZ, chiral spiro phosphonic acids and lithium hexafluoro phosphate mole
Than for 1 ︰ (1 ~ 1.5) ︰ (0.002 ~ 0.003) ︰ (0.1 ~ 0.15) ︰ (0.3 ~ 0.5).
3. chirality 3-(2- pyridine according to claim 1) the visible light asymmetry of -3- aryl substitutional amine-group compound urges
It is combined to method, which is characterized in that the visible light by power is 3W, wavelength provides for the blue LED lamp of 450-455nm.
4. chirality 3-(2- pyridine according to claim 1) the visible light asymmetry of -3- aryl substitutional amine-group compound urges
Be combined to method, which is characterized in that when the column chromatographic isolation and purification eluant, eluent by n-hexane and ethyl acetate volume ratio be 80 ~
5:1 composition.
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Cited By (2)
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| CN112745257A (en) * | 2019-10-31 | 2021-05-04 | 河南大学 | (1R) -phenylamino- (2S) -2-aryl-2-nitrogen heteroaryl cyclopentane and preparation method and application thereof |
| CN112812097A (en) * | 2021-01-26 | 2021-05-18 | 河南师范大学 | Method for synthesizing 3- (2-pyridine) substituted pyrrole compound by visible light catalysis |
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| CN105949079A (en) * | 2016-05-26 | 2016-09-21 | 河南大学 | Method for preparing N-(2-formyl phenyl) N-substituted formamide derivatives by means of visible light catalysis |
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| US20050182103A1 (en) * | 2002-03-28 | 2005-08-18 | Finke Paul E. | Substituted 2,3-diphenyl pyridines |
| CN104710377A (en) * | 2013-12-13 | 2015-06-17 | 中国科学院大连化学物理研究所 | Method for synthesizing chiral amine through biomimetic asymmetric hydrogenation |
| CN105001159A (en) * | 2014-04-23 | 2015-10-28 | 中国科学院大连化学物理研究所 | Method for synthesizing chiral cyclic amine through catalyzing asymmetric hydrogenation of quinolin-3-amine by chiral phosphoric acid |
| CN105175318A (en) * | 2015-07-29 | 2015-12-23 | 张燕梅 | Synthesis method of pheniramine maleate |
| CN105949079A (en) * | 2016-05-26 | 2016-09-21 | 河南大学 | Method for preparing N-(2-formyl phenyl) N-substituted formamide derivatives by means of visible light catalysis |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112745257A (en) * | 2019-10-31 | 2021-05-04 | 河南大学 | (1R) -phenylamino- (2S) -2-aryl-2-nitrogen heteroaryl cyclopentane and preparation method and application thereof |
| CN112745257B (en) * | 2019-10-31 | 2022-03-01 | 河南大学 | (1R) -phenylamino- (2S) -2-aryl-2-nitrogen heteroaryl cyclopentane and preparation method and application thereof |
| CN112812097A (en) * | 2021-01-26 | 2021-05-18 | 河南师范大学 | Method for synthesizing 3- (2-pyridine) substituted pyrrole compound by visible light catalysis |
| CN112812097B (en) * | 2021-01-26 | 2023-01-13 | 河南师范大学 | Method for synthesizing 3- (2-pyridine) substituted pyrrole compound by visible light catalysis |
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