CN113666928A - Preparation method of novel lovaene-2N with nitrogen atoms doped on serrated edge - Google Patents
Preparation method of novel lovaene-2N with nitrogen atoms doped on serrated edge Download PDFInfo
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- 125000004433 nitrogen atom Chemical group N* 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title abstract description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims abstract description 31
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 238000006555 catalytic reaction Methods 0.000 claims abstract 2
- 230000035484 reaction time Effects 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 9
- 230000008569 process Effects 0.000 abstract description 8
- 230000018044 dehydration Effects 0.000 abstract description 4
- 238000006297 dehydration reaction Methods 0.000 abstract description 4
- 238000007363 ring formation reaction Methods 0.000 abstract description 4
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract description 2
- 150000002466 imines Chemical group 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract description 2
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000008204 material by function Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- ZVQXQPNJHRNGID-UHFFFAOYSA-N tetramethylsuccinonitrile Chemical compound N#CC(C)(C)C(C)(C)C#N ZVQXQPNJHRNGID-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 13
- 239000003960 organic solvent Substances 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- 239000007832 Na2SO4 Substances 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 11
- 238000010791 quenching Methods 0.000 description 11
- 230000000171 quenching effect Effects 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000013076 target substance Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000001254 matrix assisted laser desorption--ionisation time-of-flight mass spectrum Methods 0.000 description 1
- 238000005442 molecular electronic Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to the technical field of photoelectric organic functional materials, and particularly discloses a preparation method of novel nitrogen atom doped oval-2N on a sawtooth-shaped edge, wherein the structure of the compound is nitrogen-doped six-membered sawtooth-shaped edge condensed ring aromatic hydrocarbon, and the compound has a two-dimensional planar structure and a conjugated system, and Bisanthene-2CHO and azidotrimethylsilane (TMSN) are used for preparing the compound3) Under the catalysis of trifluoromethanesulfonic acid (TfOH), trifluoroacetic acid (TFA) is taken as a solvent, and the catalyst is obtained through one step of processes such as dehydration, denitrification, Friedel-Crafts reaction, electrophilic cyclization and the like. The reaction equation is as follows:
Description
The invention relates to a preparation method of novel Ovalene-2N with nitrogen atoms doped on sawtooth-shaped edges.
Background
The all-carbon Organic polycyclic aromatic hydrocarbon can be regarded as a two-dimensional graphene segment, has a large delocalized pi conjugated system, generally shows pi-pi interaction in the arrangement of molecules in a crystal, has ordered accumulation and remarkable advantages in the aspect of Organic photoelectric performance, and has wide application prospects in the fields of Organic photoelectric devices (OFET), Organic Solar Cells (OSC), Organic Light-Emitting diodes (OLED), biological probes, stimulus-response materials and the like. However, the material is often greatly limited in the aspects of stability, solubility, controllable adjustment of electronic characteristics and the like, the application value of the material is influenced to a great extent, and introduction of heteroatoms at the edge of the molecular structure of the material is one of the strategies for solving the problems. Polycyclic aromatic hydrocarbons with a zigzag-shaped edge (zig-zag) structure often have an edge state of spin-polarized electrons, and can be used as a key factor for molecular electronics regulation. Aiming at the problems, the invention introduces nitrogen atoms to the edges of the zigzag edge condensed ring aromatic hydrocarbon to form a conjugated molecular skeleton containing the nitrogen atoms, can obviously improve the stability and the assembly performance of the material, can further carry out multifunctional modification on the material, and realizes the adjustability and the performance diversification of the molecular organic photoelectric molecule. The reaction of the invention is completed in one step, the separation and purification process is simple, the operation is easy, the organic solvent consumption is less, the product purity is high, and the invention is beneficial to realizing large-scale production and industrial application.
Disclosure of Invention
In order to improve the stability of the polymer, realize the controllability of photoelectric properties and expand the application value of the material, Bisanthene-2CHO and azidotrimethylsilane (TMSN) are used in the invention3) The compound is prepared by taking trifluoroacetic acid (TFA) as a solvent under the action of trifluoromethanesulfonic acid (TfOH) through one step of processes such as dehydration, denitrification, Friedel-Crafts reaction, electrophilic cyclization and the like, and the reaction equation is as follows:
the invention has the advantages that: the novel Ovalene-2N synthetic process with the nitrogen atoms doped on the sawtooth-shaped edge is completed in one step through one-pot reaction in the processes of dehydration, denitrification, electrophilic cyclization and the like, and the process is simple; the molecular structure can realize the controllability of the organic photoelectric molecule, and the hexatomic ring imine structure is easy to be subjected to multifunctional modification and is expected to endow more specific properties. The synthesis method is simple, has low cost, is beneficial to realizing industrial production, and has practical application value in the aspect of photoelectric materials.
Step one, according to the mass ratio, Bisanthene-2 CHO: azidotrimethylsilane: mixing trifluoromethanesulfonic acid =1:2:5 in trifluoroacetic acid, and stirring to react at 60 ℃ for 12 h;
step two, adding water and ethyl acetate into the reaction liquid obtained in the step one, extracting for 3 times, and combining organic phases; the volume ratio of water to ethyl acetate is 1: 3;
and step three, drying the organic phase obtained in the step two by using anhydrous sodium sulfate, filtering, adding chromatographic silica gel into the filtrate, and removing the organic solvent by reduced pressure distillation to obtain a mixture of the chromatographic silica gel and the target substance. Wherein the mass of the chromatographic silica gel is 30-40 times of the mass of the solute in the filtrate;
and step four, slowly pouring the mixture of the chromatographic silica gel obtained in the step three and the target substance into the filled chromatographic silica gel column, taking petroleum ether and ethyl acetate with the volume ratio of 2:1 as a developing agent, and separating after column chromatography to obtain the target substance.
Drawings
1. FIG. 1 is the NMR spectrum of the product.
2. FIG. 2 is the NMR carbon spectrum of the product.
3. FIG. 3 is a UV absorption spectrum of the product.
4. FIG. 4 shows fluorescence emission spectrum of the product.
5. FIG. 5 is a MALDI-TOF mass spectrum of the product.
6. FIG. 6 is a single crystal diagram of the product.
Detailed Description
Example 1
127.25 mg (0.2 mmol) of Bisanthene-2CHO, 46.08mg (0.4 mmol) of azidotrimethylsilane (TMSN)3) Adding 75.04 mg (0.5 mmol) of trifluoromethanesulfonic acid (TfOH) into 3.0 mL of trifluoroacetic acid (TFA), reacting for 4h at 60 ℃, adding 3 mL of 2 mol/L NaOH aqueous solution for quenching, extracting with 10 mL of ethyl acetate for three times, combining organic phases, and adding anhydrous Na2SO4Drying, filtering, distilling under reduced pressure to remove organic solvent, slowly pouring into packed chromatographic silica gel column, and mixing with petroleum ether and ethyl acetatePerforming column chromatography with the volume ratio of 2:1 to obtain 15.27 mg of the target compound with the yield of 12 percent.
Example 2
127.25 mg (0.2 mmol) of Bisanthene-2CHO, 46.08mg (0.4 mmol) of azidotrimethylsilane (TMSN)3) Adding 150.08mg (1.0 mmol) of trifluoromethanesulfonic acid (TfOH) into 3.0 mL of trifluoroacetic acid (TFA), reacting for 4h at 60 ℃, adding 3 mL of 2 mol/L NaOH aqueous solution for quenching, extracting with 10 mL of ethyl acetate for three times, combining organic phases, and adding anhydrous Na2SO4Drying, filtering, distilling under reduced pressure to remove organic solvent, slowly pouring into the packed chromatographic silica gel column, performing column chromatography according to the volume ratio of petroleum ether to ethyl acetate of 2:1, and separating to obtain the target compound 36.90 mg with the yield of 29%.
Example 3
127.25 mg (0.2 mmol) of Bisanthene-2CHO, 46.08mg (0.4 mmol) of azidotrimethylsilane (TMSN)3) Adding 225.12mg (1.5 mmol) of trifluoromethanesulfonic acid (TfOH) into 3.0 mL of trifluoroacetic acid (TFA), reacting for 4h at 60 ℃, adding 3 mL of 2 mol/L NaOH aqueous solution for quenching, extracting with 10 mL of ethyl acetate for three times, combining organic phases, and adding anhydrous Na2SO4Drying, filtering, distilling under reduced pressure to remove organic solvent, slowly pouring into packed chromatographic silica gel column, performing column chromatography according to the volume ratio of petroleum ether to ethyl acetate of 2:1, and separating to obtain the target compound 29.27 mg with a yield of 23%.
Example 4
127.25 mg (0.2 mmol) of Bisanthene-2CHO, 46.08mg (0.4 mmol) of azidotrimethylsilane (TMSN)3) Adding 150.08mg (1.0 mmol) of trifluoromethanesulfonic acid (TfOH) into 3.0 mL of trifluoroacetic acid (TFA), reacting for 4h at 50 ℃, adding 3 mL of 2 mol/L NaOH aqueous solution for quenching, extracting with 10 mL of ethyl acetate for three times, combining organic phases, and adding anhydrous Na2SO4Drying, filtering, distilling under reduced pressure to remove organic solvent, slowly pouring into the packed chromatographic silica gel column, performing column chromatography according to the volume ratio of petroleum ether to ethyl acetate of 2:1, and separating to obtain the target compound 31.81 mg with a yield of 25%.
Example 5
127.25 mg (0.2 mmol) of Bisanthene-2CHO, 46.08mg (0.4 mmol) of azidotrimethylsilane (TMSN)3) Adding 150.08mg (1.0 mmol) of trifluoromethanesulfonic acid (TfOH) into 3.0 mL of trifluoroacetic acid (TFA), reacting for 4h at 70 ℃, adding 3 mL of 2 mol/L NaOH aqueous solution for quenching, extracting with 10 mL of ethyl acetate for three times, combining organic phases, and adding anhydrous Na2SO4Drying, filtering, distilling under reduced pressure to remove organic solvent, slowly pouring into the packed chromatographic silica gel column, performing column chromatography according to the volume ratio of petroleum ether to ethyl acetate of 2:1, and separating to obtain the target compound 26.72 mg with a yield of 21%.
Example 6
127.25 mg (0.2 mmol) of Bisanthene-2CHO, 46.08mg (0.4 mmol) of azidotrimethylsilane (TMSN)3) Adding 150.08mg (1.0 mmol) of trifluoromethanesulfonic acid (TfOH) into 3.0 mL of trifluoroacetic acid (TFA), reacting for 4h at 80 ℃, adding 3 mL of 2 mol/L NaOH aqueous solution for quenching, extracting with 10 mL of ethyl acetate for three times, combining organic phases, and adding anhydrous Na2SO4Drying, filtering, distilling under reduced pressure to remove organic solvent, slowly pouring into the packed chromatographic silica gel column, performing column chromatography according to the volume ratio of petroleum ether to ethyl acetate of 2:1, and separating to obtain the target compound 19.09 mg with the yield of 15%.
Example 7
127.25 mg (0.2 mmol) of Bisanthene-2CHO, 46.08mg (0.4 mmol) of azidotrimethylsilane (TMSN)3) Adding 150.08mg (1.0 mmol) of trifluoromethanesulfonic acid (TfOH) into 3.0 mL of trifluoroacetic acid (TFA), reacting for 6h at 60 ℃, adding 3 mL of 2 mol/L NaOH aqueous solution for quenching, extracting with 10 mL of ethyl acetate for three times, combining organic phases, and adding anhydrous Na2SO4Drying, filtering, distilling under reduced pressure to remove organic solvent, slowly pouring into the packed chromatographic silica gel column, performing column chromatography according to the volume ratio of petroleum ether to ethyl acetate of 2:1, and separating to obtain the target compound 45.81 mg with the yield of 36%.
Example 8
127.25 mg (0.2 mmol) of Bisanthene-2CHO, 46.08mg (0.4 mmol) azidotrimethylsilane (TMSN)3) Adding 150.08mg (1.0 mmol) of trifluoromethanesulfonic acid (TfOH) into 3.0 mL of trifluoroacetic acid (TFA), reacting for 8 h at 60 ℃, adding 3 mL of 2 mol/L NaOH aqueous solution for quenching, extracting with 10 mL of ethyl acetate for three times, combining organic phases, and adding anhydrous Na2SO4Drying, filtering, distilling under reduced pressure to remove organic solvent, slowly pouring into the packed chromatographic silica gel column, performing column chromatography according to the volume ratio of petroleum ether to ethyl acetate of 2:1, and separating to obtain the target compound 52.17 mg with a yield of 41%.
Example 9
127.25 mg (0.2 mmol) of Bisanthene-2CHO, 46.08mg (0.4 mmol) of azidotrimethylsilane (TMSN)3) Adding 150.08mg (1.0 mmol) of trifluoromethanesulfonic acid (TfOH) into 3.0 mL of trifluoroacetic acid (TFA), reacting for 10 h at 60 ℃, adding 3 mL of 2 mol/L NaOH aqueous solution for quenching, extracting with 10 mL of ethyl acetate for three times, combining organic phases, and adding anhydrous Na2SO4Drying, filtering, distilling under reduced pressure to remove organic solvent, slowly pouring into packed chromatographic silica gel column, performing column chromatography according to the volume ratio of petroleum ether to ethyl acetate of 2:1, and separating to obtain the target compound 61.08 mg with a yield of 48%.
Example 10
127.25 mg (0.2 mmol) of Bisanthene-2CHO, 46.08mg (0.4 mmol) of azidotrimethylsilane (TMSN)3) Adding 150.08mg (1.0 mmol) of trifluoromethanesulfonic acid (TfOH) into 3.0 mL of trifluoroacetic acid (TFA), reacting for 12h at 60 ℃, adding 3 mL of 2 mol/L NaOH aqueous solution for quenching, extracting with 10 mL of ethyl acetate for three times, combining organic phases, and adding anhydrous Na2SO4Drying, filtering, distilling under reduced pressure to remove organic solvent, slowly pouring into the packed chromatographic silica gel column, performing column chromatography according to the volume ratio of petroleum ether to ethyl acetate of 2:1, and separating to obtain the target compound 67.44 mg with the yield of 53%.
Example 11
127.25 mg (0.2 mmol) of Bisanthene-2CHO, 46.08mg (0.4 mmol) of azidotrimethylsilane (TMSN)3) And 150.08mg (1.0)mmol) trifluoromethanesulfonic acid (TfOH), adding the trifluoromethanesulfonic acid (TfOH) into 3.0 mL trifluoroacetic acid (TFA), reacting for 14 h at 60 ℃, adding 3 mL of 2 mol/L NaOH aqueous solution, quenching, extracting with 10 mL of ethyl acetate for three times, combining organic phases, and adding anhydrous Na2SO4Drying, filtering, distilling under reduced pressure to remove organic solvent, slowly pouring into the packed chromatographic silica gel column, performing column chromatography according to the volume ratio of petroleum ether to ethyl acetate of 2:1, and separating to obtain the target compound 52.17 mg with a yield of 41%.
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of the product;1H NMR (500 MHz, CDCl3): δ (ppm) 10.69 (s, 2H), 9.32 (d, J = 10.0 Hz, 2H), 9.13 (d, J = 5.0 Hz, 2H), 9.06 (d, J = 5.0 Hz, 2H), 8.83(d, J= 10.0 Hz, 2H), 7.41 (s, 4H), 2.68 (s, 6H), 1.92 (s, 12H). fig. 2 is the nuclear magnetic resonance carbon spectrum of the product;13C NMR (125 MHz, CDCl3): δ (ppm) 147.88, 144.92, 138.31, 138.28, 138.16, 138.13, 138.08, 134.75, 134.35, 130.29, 129.56, 129.24, 128.93, 128.87, 128.82, 126.99, 126.93, 126.61, 125.28, 122.48, 121.89, 119.93, 119.07, 116.28, 21.47, 20.58, 20.54, 20.49,1.03。
Claims (2)
1. the method of claim 1, wherein the method comprises the following steps: reacting Bisanthene-2CHO with azidotrimethylsilane under the catalysis of trifluoromethanesulfonic acid to obtain a target compound, wherein the mass ratio of Bisanthene-2 CHO: azidotrimethylsilane: trifluoromethanesulfonic acid =1:2: 5.
2. The method for preparing Ovalene-2N with zigzag edges doped with nitrogen atoms as claimed in claim 2, wherein the reaction temperature is controlled at 60 ℃ during the reaction process, and the reaction time is 12 h.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114853654A (en) * | 2022-04-17 | 2022-08-05 | 内蒙古大学 | Preparation method of pyrrole ring-doped bisantene |
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| CN110156721A (en) * | 2019-05-16 | 2019-08-23 | 华南理工大学 | Utilize diazotate, cyclic ethers, amine and CO2The method of synthesis of carbamates |
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| CN110156721A (en) * | 2019-05-16 | 2019-08-23 | 华南理工大学 | Utilize diazotate, cyclic ethers, amine and CO2The method of synthesis of carbamates |
Non-Patent Citations (2)
| Title |
|---|
| TANG, CONGHUI等: "Metal-Free Nitrogenation of 2-Acetylbiphenyls: Expeditious Synthesis of Phenanthridines", ORGANIC LETTERS, vol. 17, no. 9, pages 2206 - 2209 * |
| WANG, QING等: "Cyclopenta Ring Fused Bisanthene and Its Charged Species with Open-Shell Singlet Diradical Character and Global Aromaticity/ Anti-Aromaticity", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 56, no. 38, pages 11415 - 11419 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114853654A (en) * | 2022-04-17 | 2022-08-05 | 内蒙古大学 | Preparation method of pyrrole ring-doped bisantene |
| CN114853654B (en) * | 2022-04-17 | 2024-07-09 | 内蒙古大学 | Preparation method of bisanthene doped with pyrrole ring |
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