CN116082212A - Dipyrrole compound and preparation method thereof - Google Patents
Dipyrrole compound and preparation method thereof Download PDFInfo
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- CN116082212A CN116082212A CN202310056331.6A CN202310056331A CN116082212A CN 116082212 A CN116082212 A CN 116082212A CN 202310056331 A CN202310056331 A CN 202310056331A CN 116082212 A CN116082212 A CN 116082212A
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- -1 Dipyrrole compound Chemical class 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 230000002378 acidificating effect Effects 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 15
- 238000010992 reflux Methods 0.000 claims description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 7
- 238000004440 column chromatography Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 5
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 claims description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 5
- 239000013067 intermediate product Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract description 4
- 238000006482 condensation reaction Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003446 ligand Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000005347 biaryls Chemical group 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/50—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention discloses a dipyrrole compound and a preparation method thereof, wherein the dipyrrole compound is prepared by taking 1, 4-diketone compound and hydrazine as raw materials and carrying out condensation reaction under an acidic condition.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a dipyrrole compound and a preparation method thereof.
Background
Biaryl backbones with atropisomerism are widely used in the design synthesis of catalysts and ligands. For example with C 2 The binaphthyl skeleton of symmetry axis has been widely used in the design synthesis of chiral phosphoric acid, chiral phosphine ligand and other various ligands and catalysts, and has achieved very excellent effects (G.Bringmann, M.Breuning, et al chem. Rev.2011,111,563; f.colbert, et al chem. Soc. Rev.2015,44,3418), but many reactions still cannot be achieved by the presently known ligands and catalysts. The development of new, more efficient ligands and catalysts remains the focus of current research.
As a more electron-rich and spatially tunable heteroaromatic pyrrole, it is very rare in the design synthesis of ligands and catalysts. The main reason for this is that the lack of a suitable method for preparing the desired bipyrrole backbone limits its use in the design synthesis of catalysts and ligands.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a dipyrrole compound.
Another object of the present invention is to provide a process for producing the above-mentioned dipyrrole compound.
The aim of the invention is achieved by the following technical scheme.
A dipyrrole compound has a structural formula shown in 1a or 1 b:
wherein R is 1 、R 4 、R 5 And R is 8 Each independently, is an alkyl or aryl group; r is R 2 、R 3 、R 6 And R is 7 Each independently, is hydrogen, alkyl, aryl, ester, or acyl.
The preparation method of the bipyrrole compound shown in the structural formula 1a comprises the following steps: mixing a first compound, hydrazine hydrochloride, anhydrous magnesium sulfate and a first solvent under an acidic condition, refluxing, cooling to room temperature of 20-25 ℃, decompressing and steaming to remove the first solvent, dissolving with water, extracting with ethyl acetate, washing an organic phase obtained by extraction with saturated saline, removing water, and separating by column chromatography to obtain a dipyrrole compound shown as a structural formula 1a, wherein the structural formula of the first compound is shown as a structural formula 3 a:
the acidic condition is achieved by adding a first acidic substance which is o-sulfonylbenzoyl imine, citric acid or diphenyl phosphate.
The reaction process of the preparation method of the dipyrrole compound shown in the structural formula 1a is as follows:
in the technical scheme, the ratio of the first compound to the hydrazine hydrochloride is 0.1:0.1 according to the parts by weight of the substances.
In the above technical scheme, the ratio of the parts by weight of the first compound to the parts by weight of the anhydrous magnesium sulfate is 0.1:24, the parts by weight of the first compound are in mmol, and the parts by weight are in mg.
In the above technical scheme, the first solvent is isopropanol, and the ratio of the parts by weight of the first compound to the parts by volume of the first solvent is 0.1:2, wherein the volume fraction is in mL.
In the technical scheme, the temperature of the reflux is 100-120 ℃, and the time of the reflux is at least 24 hours.
In the technical scheme, the water removal is carried out by adding anhydrous sodium sulfate and filtering.
In the technical scheme, the ratio of the first compound to the first acidic substance is 0.1:0.01 according to the parts by weight of the substances.
The preparation method of the bipyrrole compound shown in the structural formula 1a or 1b comprises the following steps:
1) Mixing a first compound, hydrazine hydrate, trifluoroacetic acid, anhydrous magnesium sulfate and a second solvent, refluxing, cooling to room temperature of 20-25 ℃, and separating by column chromatography to obtain an intermediate product, wherein the structural formula of the first compound is shown as 3 a:
in the step 1), the intermediate product has the following structural formula:
in the step 1), the ratio of the parts by weight of the first compound, the parts by weight of the hydrazine hydrate, the parts by weight of the trifluoroacetic acid, the parts by weight of anhydrous magnesium sulfate and the parts by volume of the second solvent is 0.1:1:0.02:100:2, the parts by weight of the first compound are in mmol, the parts by weight are in mg, and the parts by volume are in mL.
In the step 1), the temperature of the reflux is 110-130 ℃, and the time of the reflux is at least 24 hours.
In the step 1), the second solvent is cyclohexane.
2) Mixing a second compound, an intermediate product, a second acidic substance, anhydrous magnesium sulfate and a third solvent, reacting at room temperature, and separating by column chromatography to obtain the dipyrrole compound, wherein when the structural formula of the second compound is the same as that of the first compound, the dipyrrole compound shown as the structural formula 1a is obtained; when the structural formula of the second compound is:
in this case, the dipyrrole compound represented by the structural formula 1b is obtained.
The reaction process of the preparation method of the bipyrrole compound shown in the structural formula 1a or 1b is as follows:
in the step 2), the ratio of the parts by weight of the second compound, the intermediate, the second acidic substance, the anhydrous magnesium sulfate and the third solvent is 0.1:0.1:0.01:200:2.
In the step 2), the third solvent is toluene.
In the step 2), the room temperature reaction time is at least 24 hours.
In the step 2), the second acidic substance is a protonic acid or a lewis acid, and the second acidic substance is p-toluenesulfonic acid, acetic acid, hydrochloric acid or aluminum chloride.
The preparation method takes the 1, 4-diketone compound and the hydrazine as raw materials and carries out condensation reaction under acidic conditions, and the whole preparation process is simple and efficient, is easy to operate, and has the advantages of high repeatability, high yield and the like.
Detailed Description
The technical scheme of the invention is further described below with reference to specific embodiments.
Example 1
Bipyrroles as shown in the formula 1aA process for the preparation of a compound comprising the steps of: 24.8 mg of 1, 4-dione 3a' (0.1 mmol), hydrazine hydrochloride (10.4 mg, 0.1 mmol), sulfonylbenzoylimine (1.8 mg, 0.01mmol, phthalimide) and anhydrous magnesium sulfate (24 mg) were weighed into a 5mL single-necked round bottom flask containing a magnetic stirrer, 2mL of isopropyl alcohol was added, a reflux condenser was connected to the flask, and the mixture was reacted at 110℃for 24 hours. After the reaction was completed, the temperature of the reaction system was lowered to 20 to 25℃and isopropanol was distilled off under reduced pressure, and the obtained residue was dissolved in water (5 mL) and extracted 3 times with ethyl acetate (15 mL). The organic phases were combined, washed with saturated brine (15 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate concentrated and separated by column chromatography on silica gel (eluting with petroleum ether/ethyl acetate volume ratio 20:1) to give 1a'.34.3 mg, 75% yield as pale yellow oily liquid. The nuclear magnetic data are: 1 H NMR(500MHz,CDCl 3 ):δ7.02-7.00(m,4H),6.93-6.91(m,4H),6.87(s,2H),3.84(s,6H),2.27(s,6H),2.11(s,6H).
example 2
The preparation method of the bipyrrole compound shown in the structural formula 1a' comprises the following steps:
1) 24.8 mg of 1, 4-dione 3a' (0.1 mmol), hydrazine hydrate (1.0 mmol), trifluoroacetic acid (0.02 mmol) and anhydrous magnesium sulfate (100 mg) were weighed into a 10 mL-tube-sealed with a magnetic stirrer, 2mL of cyclohexane was added, and the mixture was reacted at 120℃for 24 hours. After the reaction, the system is cooled to room temperature, and is directly separated by silica gel column chromatography (eluting with petroleum ether/ethyl acetate volume ratio of 15:1) to obtain 2'.17.3 mg, 71% yield, white solid. The nuclear magnetic data are: 1 H NMR(500MHz,CDCl 3 ):δ7.36-7.35(m,2H),7.22(d,J＝7.5Hz,2H),6.53(d,J＝1.0Hz,1H),4.43(s,2H),3.80(d,J＝1.0Hz,3H),2.60(d,J＝0.5Hz,3H),2.39(s,3H).
2) 24.4 mg of nitrogen-aminopyrrole 2 '(0.1 mmol), 1, 4-dione 3a' (24.8 mg, 0.1 mmol), p-toluenesulfonic acid (1.7 mg, 0.01 mmol) and anhydrous magnesium sulfate (200 mg) were weighed into a 10mL reaction flask containing a magnetic stirrer, 2mL of toluene was added, and reacted at room temperature for 24 hours. After the reaction, separating by silica gel column chromatography (eluting with petroleum ether/ethyl acetate volume ratio 15:1) to obtain 2'.44.2 mg, 97% yield, white solid. The nuclear magnetic data are: 1 H NMR(500MHz,CDCl 3 ):δ7.02-7.00(m,4H),6.93-6.91(m,4H),6.87(s,2H),3.84(s,6H),2.27(s,6H),2.11(s,6H).
the foregoing has described exemplary embodiments of the invention, it being understood that any simple variations, modifications, or other equivalent arrangements which would not unduly obscure the invention may be made by those skilled in the art without departing from the spirit of the invention.
Claims (10)
1. The dipyrrole compound is characterized by having a structural formula shown in 1a or 1 b:
wherein R is 1 、R 4 、R 5 And R is 8 Each independently, is an alkyl or aryl group; r is R 2 、R 3 、R 6 And R is 7 Each independently, is hydrogen, alkyl, aryl, ester, or acyl.
2. The method for preparing the bipyrrole compound represented by structural formula 1a according to claim 1, comprising the steps of: mixing a first compound, hydrazine hydrochloride, anhydrous magnesium sulfate and a first solvent under an acidic condition, refluxing, cooling to room temperature of 20-25 ℃, decompressing and steaming to remove the first solvent, dissolving with water, extracting with ethyl acetate, washing an organic phase obtained by extraction with saturated saline, removing water, and separating by column chromatography to obtain a dipyrrole compound shown as a structural formula 1a, wherein the structural formula of the first compound is shown as a structural formula 3 a:
the acidic condition is achieved by adding a first acidic substance which is o-sulfonylbenzoyl imine, citric acid or diphenyl phosphate.
3. The preparation method according to claim 2, wherein the ratio of the first compound to the hydrazine hydrochloride is 0.1:0.1 in terms of parts by weight of the substances;
the ratio of the parts by weight of the first compound to the parts by weight of the anhydrous magnesium sulfate is 0.1:24, the parts by weight of the first compound are in mmol, and the parts by weight are in mg.
4. The method according to claim 3, wherein the first solvent is isopropyl alcohol, and the ratio of the parts by weight of the first compound to the parts by volume of the first solvent is 0.1:2, wherein the volume fraction is in mL.
5. The method according to claim 4, wherein the temperature of the reflux is 100 to 120 ℃, and the time of the reflux is at least 24 hours.
6. The method according to claim 5, wherein the removal of water is carried out by adding anhydrous sodium sulfate and filtering;
the ratio of the first compound to the first acidic substance is 0.1:0.01 in parts by weight of the substances.
7. The method for preparing the bipyrrole compound represented by structural formula 1a or 1b according to claim 1, comprising the steps of:
1) Mixing a first compound, hydrazine hydrate, trifluoroacetic acid, anhydrous magnesium sulfate and a second solvent, refluxing, cooling to room temperature of 20-25 ℃, and separating by column chromatography to obtain an intermediate product, wherein the structural formula of the first compound is shown as 3 a:
2) Mixing a second compound, an intermediate product, a second acidic substance, anhydrous magnesium sulfate and a third solvent, reacting at room temperature, and separating by column chromatography to obtain the dipyrrole compound, wherein when the structural formula of the second compound is the same as that of the first compound, the dipyrrole compound shown as the structural formula 1a is obtained; when the structural formula of the second compound is:
in this case, the dipyrrole compound represented by the structural formula 1b is obtained.
8. The production method according to claim 7, wherein in the step 1), the ratio of the parts by weight of the first compound, the parts by weight of the hydrazine hydrate, the parts by weight of the trifluoroacetic acid, the parts by weight of anhydrous magnesium sulfate and the parts by volume of the second solvent is 0.1:1:0.02:100:2, the parts by weight of the parts are in mmol, the parts by weight are in mg, and the parts by volume are in mL;
in the step 1), the temperature of the reflux is 110-130 ℃, and the time of the reflux is at least 24 hours;
in the step 1), the second solvent is cyclohexane.
9. The production method according to claim 8, wherein in the step 2), the ratio of the parts by weight of the second compound, the parts by weight of the intermediate, the parts by weight of the second acidic substance, the parts by weight of anhydrous magnesium sulfate, and the parts by volume of the third solvent is 0.1:0.1:0.01:200:2;
in the step 2), the third solvent is toluene.
10. The method of claim 9, wherein in step 2), the room temperature reaction time is at least 24 hours;
in the step 2), the second acidic substance is a protonic acid or a lewis acid, and the second acidic substance is p-toluenesulfonic acid, acetic acid, hydrochloric acid or aluminum chloride.
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| CN114524701A (en) * | 2022-01-25 | 2022-05-24 | 江苏师范大学 | N-axis chiral pyrrole derivative and synthesis method thereof |
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| CN114524701A (en) * | 2022-01-25 | 2022-05-24 | 江苏师范大学 | N-axis chiral pyrrole derivative and synthesis method thereof |
Non-Patent Citations (4)
| Title |
|---|
| MATT MCLEOD，ET AL.: "Synthetic Application of Monoprotected Hydrazines toward the Synthesis of 1-Aminopyrroles", 《J. ORG. CHEM.》, vol. 61, no. 3, 31 December 1996 (1996-12-31), pages 1180 - 1183 * |
| NORBERT KUHN，ET AL.: "Synthesis, oxidation and protonation of octamethyl-1, 1-bipyrrole", 《J. CHEM. SOC., PERKIN TRANS.》, vol. 2, 28 January 2000 (2000-01-28), pages 353 - 363 * |
| QI XU，ET AL.: "Cu(I)-Catalyzed Asymmetric Arylation of Pyrroles with Diaryliodonium Salts toward the Synthesis of N−N Atropisomers", 《ORG. LETT.》, vol. 24, 22 April 2022 (2022-04-22), pages 3138 - 3143 * |
| YARU GAO，ET AL.: "Atroposelective Synthesis of 1, 1’-Bipyrroles Bearing a Chiral N-N Axis: Chiral Phosphoric Acid Catalysis with Lewis Acid Induced Enantiodivergence", 《ANGEW. CHEM. INT. ED.》, vol. 61, 24 February 2022 (2022-02-24), pages 202200371 * |
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