CN106866488B - A kind of synthetic method of the fluoro- 4- pyrroline-2-one compound of 3,3- bis- - Google Patents
A kind of synthetic method of the fluoro- 4- pyrroline-2-one compound of 3,3- bis- Download PDFInfo
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- CN106866488B CN106866488B CN201710092467.7A CN201710092467A CN106866488B CN 106866488 B CN106866488 B CN 106866488B CN 201710092467 A CN201710092467 A CN 201710092467A CN 106866488 B CN106866488 B CN 106866488B
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
The invention belongs to technical field of organic synthesis, more particularly to one kind 3, the synthetic method of the fluoro- 4- pyrroline-2-one compound of 3- bis-, it is the following steps are included: bromodifluoroethylene acetamides are dissolved with solvent, and alkynes is added and is uniformly mixed, ligand Phen, catalyst CuI and alkali K is then added2CO3, be warming up to 110 ± 10 DEG C in confined conditions and be stirred to react 1-3 hours, reaction end is post-treated to obtain the final product.The present invention is 3, the synthesis for the first time of the fluoro- 4- pyrroline-2-one derivative of 3- bis- has the characteristics that Atom economy is high, reaction step is simple, raw material is cheap and easy to get, wide application range of substrates is general, is suitable for synthesis various 3, the fluoro- 4- pyrroline-2-one compound of 3- bis-, and it is suitable for industrialized production.
Description
Technical field:
The invention belongs to chemical technical field of organic synthesis, and in particular to one kind is with alkynes and bromodifluoroethylene ethanamide
Closing object is the method that catalytic material synthesizes the fluoro- 4- pyrroline-2-one compound of 3,3- bis-.
Background technique:
Fluorine-containing heterocycles are widely used in medicine, agricultural chemicals and Material Field, the introducing of fluorine atom in heterocycle
Its bioactivity can be improved, improve stability ((a) Uneyama, K. of biomolecule; Sasaki, K.
Pharmaceuticals containing fluorinated heterocyclic compounds. In Fluorinated Heterocyclic Compounds: Synthesis, Chemistry and Application; Petrov, V. A.,
Ed.; John Wiley & Sons: Hoboken. 2009, 419. (b) Kwiatkowski, P.; Beeson, T.
D.; Conrad, J. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2011, 133, 1738. (c)
Silvester, M. J. Aldrichimica Acta. 1991, 24, 31.).Currently, some fluorine-containing heterocyclic compounds
(Filler R, Kobayashi Y, Yagupolskii L M. is applied in industrial, agricultural and pharmaceuticallyOrganofluorine Compounds in Medicinal Chemistry and Biomedical Applications. Amsterdam: Elsever, 1993.), wherein have in medicine using pyrrolin as the compound of mother nucleus structure and widely answers
With, and due to, with the presence of C=C unsaturated bond, can be used as medicine or organic synthesis intermediate, further occurrence in molecule
Function dough reaction, to being modified with for the pyrrolidones with pharmacological activity such as anti-inflammatory, anti-senile dementia, antitumor and AntiHIV1 RT activities
Important role.Fluorine atom is introduced in pyrrolin molecule will further improve the physiological activity of drug, therefore, development green
The method of environmentally friendly, the new and effective fluoro- 4- pyrroline-2-one compound of synthesis 3,3- bis- is quite important and has important medicinal
Researching value.
Up to the present, the method for synthesizing the fluoro- 4- pyrroline-2-one compound of 3,3- bis- is rarely reported.In recent years, alkynes
Bifunctional dough reaction due to can simultaneously in the molecule introduce two different groups, raw materials used simple and easy to get, atom
Economy is high, is rapidly developed in the complicated organic molecule of synthesis.Also, the product after reacting has C=C unsaturated
Key exists, and the reaction of function dough can further occur, be conducive to modify product.Therefore, development efficiently, it is cheap,
The bifunctional dough using alkynes of environmental protection reacts of crucial importance to synthesize the fluoro- 4- pyrroline-2-one compound of 3,3- bis-.
Summary of the invention:
It is an object of that present invention to provide one kind using alkynes and bromodifluoroethylene acetamides as catalytic material synthesis 3,
The method of the fluoro- 4- pyrroline-2-one compound of 3- bis-, this method is high with Atom economy, reaction step is simple, raw material is cheap
It is easy to get, the advantages that wide application range of substrates is general.
The synthetic method of the fluoro- 4- pyrroline-2-one compound of 3,3- of one kind bis- comprising following steps:
Bromodifluoroethylene acetamides are dissolved with solvent, and alkynes is added and is uniformly mixed, it is adjacent that ligand is then added
Phenanthroline (Phen), catalyst CuI and alkali K2CO3, it is warming up to 110 ± 10 DEG C in confined conditions and is stirred to react 1-3 hours, instead
Should terminate it is post-treated to obtain the final product.Reaction equation is as follows:
In formula, compound 1 is alkynes, can be phenylacetylene class compound or acetenyl that aromatic ring has various substituent groups
Thiophene compound etc., specific such as phenylacetylene, to fluorobenzene acetylene, to bromobenzene acetylene phenylacetylene class compound or 3- acetenyl thiophene
Pheno heteroaryl acetylene compound.Compound 2 is bromodifluoroethylene acetamides, can be substituted aryl, benzyl or phenethyl
Bromodifluoroethylene acetamide etc., it is specific such as bromodifluoroethylene acetyl-p-toluidine, bromodifluoroethylene acetyl -3,4- dimethoxyaniline
Or bromodifluoroethylene acetyl phenyl ethylamine etc..Solvent for use can be acetonitrile (CH3CN) etc., 1mmol bromodifluoroethylene ethanamide chemical combination
Object addition 8-15ml solvent is advisable.
Specifically, the molar ratio of the bromodifluoroethylene acetamides and alkynes is 1:1.2-1:2.0.
Specifically, the molar ratio of the ligand Phen and bromodifluoroethylene acetamides is 5-15:100, urge
The molar ratio of agent CuI and bromodifluoroethylene acetamides is 5-15:100, alkali K2CO3With bromodifluoroethylene ethanamide
The molar ratio for closing object is 1.5-2.5:1.
The method of the present invention is catalyst, Phen (Phen) for ligand using CuI, K2CO3It is carried out in acetonitrile solvent for alkali
Reaction, obtains the fluoro- 4- pyrroline-2-one of 3,3- bis- through catalytic addition one-step method by alkynes and bromodifluoroethylene acetamides
Compound.Compared to the prior art, advantages of the present invention and novelty are: 1) having filled up and be effectively synthesized the fluoro- 4- pyrrole of 3,3- bis-
The blank of quinoline -2- ketone compound method is coughed up, provides letter for its expansion application further in medicine, material and organic synthesis
Single practical synthetic method, and operation is simple, yield is higher.2) raw material used in the reaction is easily obtained from industrial products
, reagent is cheap, and substrate spectrum is wide in range, is suitable for industrial production.3) the fluoro- 4- pyrroline-2-one chemical combination of synthetic product 3,3- bis-
Object is alkenes compounds, with the presence of C=C unsaturated bond in structural formula, can be used as medicine or organic synthesis intermediate, into
The reaction of function dough occurs for one step, synthesizes the polysubstituted pyrrole alkane ketone compounds with important medical value.
Detailed description of the invention
Fig. 1 is the fluoro- 4- pyrroline-2-one 3a's of 1 product 3,3- of embodiment bis-1H NMR spectra；
Fig. 2 is the fluoro- 4- pyrroline-2-one 3a's of 1 product 3,3- of embodiment bis-13C NMR spectra；
Fig. 3 is the fluoro- 4- pyrroline-2-one 3a's of 1 product 3,3- of embodiment bis-19F NMR spectra；
Fig. 4 is the fluoro- 4- pyrroline-2-one 3f's of 6 product 3,3- of embodiment bis-1H NMR spectra；
Fig. 5 is the fluoro- 4- pyrroline-2-one 3f's of 6 product 3,3- of embodiment bis-13C NMR spectra；
Fig. 6 is the fluoro- 4- pyrroline-2-one 3f's of 6 product 3,3- of embodiment bis-19F NMR spectra.
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.
Embodiment 1:
Firstly, being put into stirrer in the seal pipe of 35 mL, and sequentially add 79.2 mg(0.3 mmol) bromodifluoroethylene
Acetyl-p-toluidine, 3.0 ml acetonitriles, 49 μ L phenylacetylenes (0.45 mmol) are uniformly mixed.Secondly, to uniformly mixed solution
In sequentially add 5.4 mg Phen(0.03 mmol), 5.7 mg CuI(0.03 mmol) and 82.9 mg K2CO3(0. 6
Mmol), tight nozzle is sealed with cock, is heated to 110 DEG C and is stirred to react 2 hours.After reaction, system is cooled to room temperature, to
3 ml distilled water are added in reaction mixture, ethyl acetate extracts (5 ml × 3), merges organic phase, and anhydrous sodium sulfate is dry, subtracts
Solvent is distilled off in pressure, and residue is through silica gel column chromatography (VPetroleum ether: VEthyl acetate=50:1) separate to obtain 78.7 mg white solid products
3a, yield 92%.Reaction sees below formula:
Spectrum elucidation data
1H NMR (400 MHz, CDCl3): δ = 2.32 (s, 3H), 5.63 (t, J = 1.2 Hz, 1H),
6.91 (d, J = 8.4 Hz, 2H), 7.11 (d, J = 8.0 Hz, 2H), 7.18 (d, J = 7.6 Hz, 2H),
7.29 (t, J = 7.6 Hz, 2H), 7.38 (t, J = 7.6 Hz, 1H); 13C NMR (100 MHz, CDCl3):δ = 21.1, 99.8 (t, J = 23.0 Hz), 112.9 (t, J = 244.0 Hz), 126.5, 127.9,
128.5, 128.8, 129.6, 130.6, 130.9, 137.9, 154.6 (t, J = 11.0 Hz), 166.9 (t, J
= 30.0 Hz); 19F NMR(376 MHz, CDCl3): δ = -110.1. HRMS(ESI-TOF)Calcd for
C17H14F2NO, [M+H]+ m/z 286.1043, Found 286.1042。
Embodiment 2:
Firstly, being put into stirrer in the seal pipe of 35 mL, and sequentially add 79.2 mg(0.3 mmol) bromodifluoroethylene
Acetyl-p-toluidine, 3.0 ml acetonitriles, 52 μ L are uniformly mixed fluorobenzene acetylene (0.45 mmol).Secondly, to uniformly mixed
5.4 mg Phen(0.03 mmol are sequentially added in solution), 5.7 mg CuI(0.03 mmol) and 82.9 mg K2CO3(0. 6
Mmol), tight nozzle is sealed with cock, is heated to 110 DEG C and is stirred to react 2 hours.After reaction, system is cooled to room temperature, to
3 ml distilled water are added in reaction mixture, ethyl acetate extracts (5 ml × 3), merges organic phase, and anhydrous sodium sulfate is dry, subtracts
Solvent is distilled off in pressure, and residue is through silica gel column chromatography (VPetroleum ether: VEthyl acetate=50:1) separate to obtain 82.9 mg white solid products
3b, yield 91%.Reaction sees below formula:
Spectrum elucidation data
1H NMR (400 MHz, CDCl3): δ = 2.33 (s, 3H), 5.61 (d, J = 1.6 Hz, 1H),
6.90 (d, J = 8.4 Hz, 2H), 6.98 (t, J = 8.4 Hz, 2H), 7.13 (d, J = 8.0 Hz, 2H),
7.16-7.20 (m, 2H); 13C NMR (100 MHz, CDCl3): δ = 21.1, 99.7 (t, J = 23.0 Hz),
112.8 (t, J = 244.0 Hz), 115.8 (d, J = 22.0 Hz), 124.9 (d, J = 3.0 Hz),
126.6, 129.8, 130.1 (d, J = 8.0 Hz), 130.8, 138.1, 153.5 (t, J = 11.0 Hz),
163.8 (d, J = 251.0 Hz), 166.7 (t, J = 30.0 Hz); 19F NMR(376 MHz, CDCl3): δ =
-110.0, -108.3. HRMS(ESI-TOF)Calcd for C17H13F3NO, [M+H]+ m/z 304,0949, Found
304,0944。
Embodiment 3:
Firstly, being put into stirrer in the seal pipe of 35 mL, and sequentially add 79.2 mg(0.3 mmol) bromodifluoroethylene
Acetyl-p-toluidine, 3.0 ml acetonitriles, 81.5 mg are uniformly mixed bromobenzene acetylene (0.45 mmol).Secondly, to being uniformly mixed
Solution in sequentially add 5.4 mg Phen(0.03 mmol), 5.7 mg CuI(0.03 mmol) and 82.9 mg K2CO3(0.
6 mmol), tight nozzle is sealed with cock, 110 DEG C is heated to and is stirred to react 2 hours.After reaction, system is cooled to room temperature,
3 ml distilled water are added into reaction mixture, ethyl acetate extracts (5 ml × 3), merges organic phase, and anhydrous sodium sulfate is dry,
Vacuum distillation removes solvent, and residue is through silica gel column chromatography (VPetroleum ether: VEthyl acetate=50:1) separate to obtain 89.6 mg white solid products
3c, yield 82%.Reaction sees below formula:
Spectrum elucidation data
1H NMR (400 MHz, CDCl3): δ= 2.33 (s, 3H), 5.64 (s, 1H), 6.90 (d, J =
8.0 Hz, 2H), 7.05 (d, J = 8.0 Hz, 2H), 7.13 (d, J = 8.0 Hz, 2H), 7.43 (d, J =
8.4 Hz, 2H); 13C NMR (100 MHz, CDCl3): δ= 21.1, 100.1 (t, J = 23.0 Hz), 112.6
(t, J = 244.0 Hz), 125.2, 126.5, 127.7, 129.4, 129.8, 130.7, 131.9, 138.2,
153.5 (t, J = 11.0 Hz), 166.7 (t, J = 30.0 Hz); 19F NMR(376 MHz, CDCl3): δ = -
110.2. HRMS(ESI-TOF)Calcd for C17H13BrF2NO, [M+H]+ m/z 364.0149, Found 364.0156。
Embodiment 4:
Firstly, being put into stirrer in the seal pipe of 35 mL, and sequentially add 79.2 mg(0.3 mmol) bromodifluoroethylene
Acetyl-p-toluidine, 3.0 ml acetonitriles, 45 μ L 3- thiophene acetylenes (0.45 mmol) are uniformly mixed.Secondly, to being uniformly mixed
Solution in sequentially add 5.4 mg Phen(0.03 mmol), 5.7 mg CuI(0.03 mmol) and 82.9 mg K2CO3(0.
6 mmol), tight nozzle is sealed with cock, 110 DEG C is heated to and is stirred to react 2 hours.After reaction, system is cooled to room temperature,
3 ml distilled water are added into reaction mixture, ethyl acetate extracts (5 ml × 3), merges organic phase, and anhydrous sodium sulfate is dry,
Vacuum distillation removes solvent, and residue is through silica gel column chromatography (VPetroleum ether: VEthyl acetate=40:1) separate to obtain 62.9 mg white solid products
3d, yield 72%.Reaction sees below formula:
Spectrum elucidation data
1H NMR (400 MHz, CDCl3): δ = 2.39 (s, 3H), 5.66 (s, 1H), 6.95 (d, J =
5.2 Hz, 1H), 6.99 (s, 1H), 7.04 (d, J = 8.0 Hz, 2H), 7.21 (d, J = 8.0 Hz,
2H), 7.28 (d, J = 2.4 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ = 21.2, 98.0 (t, J
= 23.0 Hz), 113.0 (t, J = 244.0 Hz), 126.4, 126.6, 127.3, 127.5, 129.4,
129.9, 131.1, 138.7, 149.2 (t, J = 11.0 Hz), 166.9 (t, J = 30.0 Hz); 19F NMR
(376 MHz, CDCl3): δ = -109.6. HRMS(ESI-TOF)Calcd for C15H12F2NOS, [M+H]+ m/z
292.0608, Found 292.0610。
Embodiment 5:
Firstly, being put into stirrer in the seal pipe of 35 mL, and sequentially add 93.0 mg(0.3 mmol) bromodifluoroethylene
Acetyl -3,4- dimethoxyaniline, 3.0 ml acetonitriles, 49 μ L phenylacetylenes (0.45 mmol) are uniformly mixed.Secondly, equal to mixing
5.4 mg Phen(0.03 mmol are sequentially added in even solution), 5.7 mg CuI(0.03 mmol) and 82.9 mg K2CO3
(0. 6 mmol) seals tight nozzle with cock, is heated to 110 DEG C and is stirred to react 2 hours.After reaction, system is cooled to room
3 ml distilled water are added into reaction mixture for temperature, and ethyl acetate extracts (5 ml × 3), merge organic phase, and anhydrous sodium sulfate is dry
Dry, vacuum distillation removes solvent, and residue is through silica gel column chromatography (VPetroleum ether: VEthyl acetate=40:1) separate to obtain 88.3 mg white solids
Product 3e, yield 89%.Reaction sees below formula:
Spectrum elucidation data
1H NMR (400 MHz, CDCl3): δ = 3.68 (s, 3H), 3.84 (s, 3H), 5.63 (d, J =
2.0 Hz, 1H), 6.51 (d, J = 2.4 Hz, 1H), 6.61 (dd, J 1 = 2.4 Hz, J 2 = 8.8 Hz,
1H), 6.77 (d, J = 8.4 Hz, 1H), 7.19 (t, J = 7.2 Hz, 2H), 7.29 (t, J = 7.6 Hz,
2H), 7.38 (t, J = 7.6 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ = 55.9, 55.9, 99.5
(t, J = 23.0 Hz), 110.4, 110.9, 112.8 (t, J = 244.0 Hz), 119.3, 126.3, 127.9,
128.4, 128.8, 130.5, 148.5, 149.0, 154.6 (t, J = 11.0 Hz), 166.8 (t, J = 30.0
Hz); 19F NMR(376 MHz, CDCl3): δ = -110.2. HRMS(ESI-TOF)Calcd for C18H16F2NO3, [M
+H]+ m/z 332.1098, Found 332.1096。
Embodiment 6:
Firstly, being put into stirrer in the seal pipe of 35 mL, and sequentially add 83.4 mg(0.3 mmol) bromodifluoroethylene
Acetyl phenyl ethylamine, 3.0 ml acetonitriles, 49 μ L phenylacetylenes (0.45 mmol) are uniformly mixed.Secondly, into uniformly mixed solution
Sequentially add 5.4 mg Phen(0.03 mmol), 5.7 mg CuI(0.03 mmol) and 82.9 mg K2CO3(0. 6
Mmol), tight nozzle is sealed with cock, is heated to 110 DEG C and is stirred to react 2 hours.After reaction, system is cooled to room temperature, to
3 ml distilled water are added in reaction mixture, ethyl acetate extracts (5 ml × 3), merges organic phase, and anhydrous sodium sulfate is dry, subtracts
Solvent is distilled off in pressure, and residue is through silica gel column chromatography (VPetroleum ether: VEthyl acetate=40:1) separate to obtain 56.5 mg white solid products
3f, yield 63%.Reaction sees below formula:
Spectrum elucidation data
1H NMR (400 MHz, CDCl3): δ = 2.68 (t, J = 7.2 Hz, 2H), 3.70 (t, J =
7.2 Hz, 2H), 5.33 (s, 1H), 6.91-6.93 (m, 2H), 7.20-7.26 (m, 5H), 7.43-7.53
(m, 3H); 13C NMR (100 MHz, CDCl3): δ = 34.3, 42.3, 99.7 (t, J = 23.0 Hz),
112.8 (t, J = 244.0 Hz), 126.7, 127.7, 128.6, 128.8, 128.9, 129.0, 130.6,
137.3, 154.9 (t, J = 11.0 Hz), 167.9 (t, J = 30.0 Hz); 19F NMR(376 MHz,
CDCl3): δ = -112.8. HRMS(ESI-TOF)Calcd for C18H16F2NO, [M+H]+ m/z 300.1200,
Found 300.1204。
Claims (3)
1. one kind 3, the synthetic method of the fluoro- 4- pyrroline-2-one compound of 3- bis-, which comprises the following steps:
Bromodifluoroethylene acetamides are dissolved with solvent, and alkynes is added and is uniformly mixed, ligand neighbour Féraud is then added
Quinoline, catalyst CuI and alkali K2CO3, it is warming up to 110 ± 10 DEG C in confined conditions and is stirred to react 1-3 hours, reaction terminates after
It handles to obtain the final product；
The bromodifluoroethylene acetamides are bromodifluoroethylene acetyl-p-toluidine, bromodifluoroethylene acetyl -3,4- dimethoxy
Base aniline or bromodifluoroethylene acetyl phenyl ethylamine；The alkynes be phenylacetylene, to fluorobenzene acetylene, to bromobenzene acetylene or 3- acetenyl thiophene
Pheno.
2. the synthetic method of the fluoro- 4- pyrroline-2-one compound of 3,3- bis- as described in claim 1, which is characterized in that the bromine
It is 1:1.2-1:2.0 for the molar ratio of difluoro acetamides and alkynes.
3. the synthetic method of the fluoro- 4- pyrroline-2-one compound of 3,3- bis- as described in claim 1, which is characterized in that described to match
The molar ratio of body Phen and bromodifluoroethylene acetamides is 5-15:100, catalyst CuI and bromodifluoroethylene acetyl
The molar ratio of aminated compounds is 5-15:100, alkali K2CO3Molar ratio with bromodifluoroethylene acetamides is 1.5-
2.5:1.
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| CN105367481A (en) * | 2015-12-03 | 2016-03-02 | 河南工程学院 | Synthetic method for 3,3-difluoro-2-oxindole derivative |
| CN106008304A (en) * | 2016-05-18 | 2016-10-12 | 湖北科技学院 | 1,3-dihydro-2H-pyrrolidone compounds and synthetic method thereof |
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|---|---|---|---|---|
| CN105367481A (en) * | 2015-12-03 | 2016-03-02 | 河南工程学院 | Synthetic method for 3,3-difluoro-2-oxindole derivative |
| CN106008304A (en) * | 2016-05-18 | 2016-10-12 | 湖北科技学院 | 1,3-dihydro-2H-pyrrolidone compounds and synthetic method thereof |
Non-Patent Citations (2)
| Title |
|---|
| Copper-catalyzed cascade coupling/cyclization of terminal alkynes with diazoacetates: a straightforward route for trisubstituted furans;Lei Zhou et al.,;《Tetrahedron Letters》;20110816;第52卷;第5484-5487页 |
| Zhishi Ye et al.,.Copper-Catalyzed Cyclopropanol Ring Opening Csp3−Csp3 Cross-Couplings with (Fluoro)Alkyl Halides.《Org. Lett.》.2015,第17卷 |
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