CN111057046B - Isoindole tetrapyrrole pigment and preparation method thereof - Google Patents
Isoindole tetrapyrrole pigment and preparation method thereof Download PDFInfo
- Publication number
- CN111057046B CN111057046B CN201911273748.8A CN201911273748A CN111057046B CN 111057046 B CN111057046 B CN 111057046B CN 201911273748 A CN201911273748 A CN 201911273748A CN 111057046 B CN111057046 B CN 111057046B
- Authority
- CN
- China
- Prior art keywords
- isoindole
- contact reaction
- tetrapyrrole
- alkali
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention relates to the fields of organic synthesis and fine chemical preparation, and discloses an isoindole tetrapyrrole pigment and a preparation method thereof, wherein the preparation method comprises the following steps: mixing isoindolinone shown in a formula (A), pyrrole shown in a formula (B) or a derivative thereof with a solvent, and carrying out a first contact reaction under an acidic condition; then, carrying out alkali treatment for second contact reaction;
solves the problems of limited synthesis, more steps, noble metal catalysis, noble raw materials, harsh reaction conditions and the like of the chemical synthesis method of conjugated tetrapyrrole derivatives and analogues in the prior art.
Description
Technical Field
The invention relates to the fields of organic synthesis and fine chemical preparation, in particular to an isoindole tetrapyrrole pigment and a preparation method thereof.
Background
Tetrapyrrole derivatives have important applications in biomedical and materials science fields, such as porphyrin derivatives, chlorophyll, iron oxide red, etc. The tetrapyrroles developed at present are mostly formed by connecting pyrrole by a carbon bond bridge. However, due to the lengthy and complex synthetic steps of polypyrrole, the conjugated polypyrrole backbone developed in recent years is not large. The 2,2' -dipyrrole is a key precursor of a large amount of anticancer drugs such as prodigiosin and extended porphyrin. The linear tetrapyrroles reported to date are generally obtained by condensing dipyrrole and triethyl orthoformate under acidic conditions. Although there have been some methods for constructing directly linked 2,2' -bipyrroles, such as oxidative coupling of alfa-site pyrrole, carnot cyclocondensation, ullmann coupling, and other metal catalyzed couplings, the synthesis of such bipyrroles currently has significant challenges, especially for the construction of asymmetric bipyrroles. Therefore, the development of a novel synthetic method of the tetrapyrrole skeleton is urgent and has practical significance.
In the prior art, the chemical synthesis method of conjugated tetrapyrrole derivatives and analogues has the defects of limited synthesis, more steps, noble metal catalysis, noble raw materials, harsh reaction conditions, high difficulty due to the requirement of noble metal palladium-catalyzed Suzuki coupling, generally high cost of 1-N-Boc pyrrole boric acid, limited substrate application range and difficult commercialization.
Therefore, the method for synthesizing the tetrapyrrole by using the practical method with simple steps and easily available raw materials is a problem to be solved in the invention.
Disclosure of Invention
The invention aims to provide an isoindole tetrapyrrole pigment and a preparation method thereof, which solve the problems of limited synthesis, more steps, noble metal catalysis, noble raw materials, harsh reaction conditions and the like of a chemical synthesis method of conjugated tetrapyrrole derivatives and analogues in the prior art.
In order to achieve the above object, the present invention provides an isoindole tetrapyrrole pigment having the structure:
wherein R1, R2, R3 and R4 are each independently H, C 1 -C 12 Straight or branched alkyl, C 1 -C 12 Straight OR branched cycloalkyl groups, aromatic groups, halogen, SR5, OR5, NR5R6, NO 2 、SO 3 H、(CH 2 )nCH 2 SO 3 H、(CH 2 )nCH 2 OH、(CHOH) n CH 2 OH、(CH 2 ) n CH 2 Br、(CH 2 )nCH 2 (PPh 3 )Br、(CH 2 )nCH 2 (PPh 3 )I、(CH 2 )nCH 2 (NEt 3 )Br、(CH 2 ) n CH 2 (NEt 3 )I、(CH＝CH 2 )(C 6 H 4 ) R5 or (ch=ch) 2 )(C 6 H 4 ) One of OR 5;
r5 and R6 are each independently H, CH 2 COOEt, C1-12 linear or branched alkyl, C1-12 linear or branched cycloalkyl, aromatic group,wherein n is a positive integer.
The invention also provides a preparation method of the isoindole tetrapyrrole pigment, which comprises the following steps:
mixing isoindolinone shown in a formula (A), pyrrole or pyrrole derivative shown in a formula (B) and a solvent, and performing a first contact reaction under an acidic condition; then, carrying out alkali treatment for second contact reaction;
through the technical scheme, the invention provides the isoindole tetrapyrrole pigment and the preparation method thereof, and the invention develops a one-pot method for preparing the isoindole tetrapyrrole pigment from the cheap and easily available commercial products of isoindolinone and pyrrole derivatives, the process is simple, the reaction is efficient, and the tetrapyrrole pigment prepared by the method provided by the invention has a large size of up to 70795cm -1 Molar absorptivity, maximum absorption wavelength of 510-610nm, and maximum emission spectrum of 580-670nm.
Additional features and advantages of the invention will be set forth in the detailed description which follows.
Drawings
The accompanying drawings are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, illustrate the invention and together with the description serve to explain, without limitation, the invention. In the drawings:
FIG. 1 is a view showing the structure of an X-ray single crystal of isoindole tetrapyrrole pigment 1 a;
FIG. 2 is a view showing the structure of an X-ray single crystal of isoindole tetrapyrrole pigment 1 c;
FIG. 3 is a view showing the structure of an X-ray single crystal of isoindole tetrapyrrole pigment 1 d;
FIG. 4 is a view showing the structure of an X-ray single crystal of isoindole tetrapyrrole pigment 1 e;
FIG. 5 is an absorption spectrum of isoindole tetrapyrrole pigments 1a-f (10. Mu. Mol/L) in methylene chloride;
FIG. 6 is an emission spectrum of isoindole tetrapyrrole pigments 1a-f in methylene chloride.
Detailed Description
The following describes specific embodiments of the present invention in detail. It should be understood that the detailed description and specific examples, while indicating and illustrating the invention, are not intended to limit the invention.
The endpoints and any values of the ranges disclosed herein are not limited to the precise range or value, and are understood to encompass values approaching those ranges or values. For numerical ranges, one or more new numerical ranges may be found between the endpoints of each range, between the endpoint of each range and the individual point value, and between the individual point value, in combination with each other, and are to be considered as specifically disclosed herein.
The invention provides an isoindole tetrapyrrole pigment, which has the structure as follows:
wherein R1, R2, R3 and R4 are each independently H, C 1 -C 12 Straight or branched alkyl, C 1 -C 12 Straight OR branched cycloalkyl groups, aromatic groups, halogen, SR5, OR5, NR5R6, NO 2 、SO 3 H、(CH 2 )nCH 2 SO 3 H、(CH 2 )nCH 2 OH、(CHOH) n CH 2 OH、(CH 2 ) n CH 2 Br、(CH 2 )nCH 2 (PPh 3 )Br、(CH 2 )nCH 2 (PPh 3 )I、(CH 2 )nCH 2 (NEt 3 )Br、(CH 2 ) n CH 2 (NEt 3 )I、(CH＝CH 2 )(C 6 H 4 ) R5 or (ch=ch) 2 )(C 6 H 4 ) One of OR 5;
x is NH, NR5, O, S;
r5 and R6 are each independently H, CH 2 COOEt, C1-12 straight or branched chainAlkyl, C1-12 linear or branched cycloalkyl group, aromatic group, wherein n is a positive integer.
In a preferred embodiment of the invention, the halogen is one of F, cl, br or I;
the aromatic group is one of a thiophene group, a furan group or a benzene ring group.
In a preferred embodiment of the invention, R1, R2 and R3 are each independently H, C 1 -C 12 Straight or branched alkyl, C 1 -C 12 A linear OR branched cycloalkyl group, cl, a thiophene group, a furan group, a benzene ring group, OR5, NR5R6, OR SR 5;
r5 and R6 are each independently H, CH 2 COOEt, naphthyl, thienyl, C 1 -C 12 Straight or branched alkyl, C 1 -C 12 A linear or branched cycloalkyl group.
In a preferred embodiment of the invention, R1, R3 are each independently H or methyl;
r2 is each independently H or ethyl;
r4 is each independently H or C 1 -C 12 Straight or branched alkyl of (a).
The invention also provides a preparation method of the isoindole tetrapyrrole pigment, which comprises the following steps:
mixing isoindolinone shown in a formula (A), pyrrole shown in a formula (B) or a derivative thereof with a solvent, and carrying out a first contact reaction under an acidic condition; then, carrying out alkali treatment for second contact reaction;
in a preferred embodiment of the invention, the heterocyclic compound is used in an amount of 0.2 to 20mmol relative to 1mmol of isoindolinone.
In a preferred embodiment of the present invention, the conditions of the first contact reaction include: the temperature is 70-150 ℃ and the time is 2-100h;
and/or, the conditions of the second contact reaction include: the temperature is 0-120 ℃ and the time is 1-100h.
In a preferred embodiment of the present invention, the alkali treatment comprises alkali extraction and washing performed sequentially, and the alkali of the alkali treatment is provided by an organic alkali and/or an inorganic alkali;
wherein the organic base is one or more of triethylamine, N diisopropylethylamine, 1, 8-diazabicyclo [5.4.0] undec-7-ene and diethylamine;
the inorganic alkali is one or more of sodium bicarbonate and a solution thereof, potassium bicarbonate and a solution thereof, sodium carbonate and a solution thereof, and potassium carbonate, sodium hydroxide and a solution thereof, and potassium hydroxide and a solution thereof;
preferably, the pH of the system at the beginning of the second contact reaction is 7.5-14.
In a preferred embodiment of the present invention, the acidic condition is provided by a lewis acid comprising one or more of titanium tetrachloride, phosphorus oxychloride, and phosphorus oxybromide;
preferably, the pH of the system at the beginning of the first contact reaction is from 2.0 to 6.0.
In a preferred embodiment of the present invention, the solvent is one or more of chloroform, 1, 2-dichloromethane, toluene, chlorobenzene, o-dichlorobenzene, p-dichlorobenzene, m-dichlorobenzene and ethyl acetate.
The present invention will be described in detail by examples.
Example 1
Synthesis of isoindole tetrapyrrole pigment 1 a:
under the protection of nitrogen, isoindolinone (100 mg,0.75 mmol) and pyrrole (62 mu L,0.90 mmol) are dissolved in anhydrous chlorobenzene (20 mL), phosphorus oxychloride (68 mu L,0.75 mmol) is added, and the reaction mixture is heated to 110 ℃ and stirred for 6h; TLC tracking plate, after isoindolinone consumption is complete, adding sodium carbonate saturated solution containing potassium ferricyanide into the reaction system, stirring for 2 hours at room temperature, transferring the reaction mixture into a separating funnel, adding dichloromethane and water, extracting, standing, separating organic phase, extracting corresponding water phase with dichloromethane three times, and combining organic layers; the organic phase was washed once with water, dried over anhydrous sodium sulfate, filtered and the solvent concentrated in vacuo. The crude product was purified by silica gel column chromatography and recrystallized from methylene chloride and n-hexane to give isoindole tetrapyrrole pigment 1a powder. The yield of preparation 1a was 40% (54 mg).
The nuclear magnetic data and high-resolution mass spectrum data are as follows: 1 H NMR(400MHz,d 6 -DMSO)δ12.06(s,2H),9.30(d,J＝7.3Hz,2H),8.23(d,J＝7.4Hz,2H),7.62-7.53(m,4H),7.49(t,J＝2.9Hz,2H),7.35(d,J＝2.9Hz,2H),6.46(q,J＝2.7Hz,2H). 13 C NMR(101MHz,d 6 -DMSO)δ159.0,147.6,140.4,136.6,128.5,128.3,127.7,127.0,125.6,122.2,115.3,111.4.HRMS(APCI)calcd for C 24 H 17 N 4 [M+H] + :361.1453,found 361.1441。
example 2
Synthesis of isoindole tetrapyrrole pigment 1 b:
the procedure of example 1 was followed except that the equivalent amount of pyrrole was changed to 2, 4-dimethylpyrrole (77. Mu.L, 0.90 mmol), to give a yield of 1b of 46% (72 mg).
The nuclear magnetic data and high-resolution mass spectrum data are as follows: 1 H NMR(400MHz,CDCl 3 )δ9.04(d,J＝7.6Hz,2H),8.92(s,2H),7.91(d,J＝7.6Hz,2H),7.51(t,J＝7.4Hz,2H),7.43(t,J＝7.4Hz,2H),6.06(s,2H),2.68(s,6H),2.42(s,6H). 13 C NMR(101MHz,CDCl 3 )δ160.2,148.3,141.5,137.6,133.8,128.4,127.9,127.6,127.4,125.1,122.3,113.6,15.1,13.7.HRMS(APCI)calcd for C 28 H 25 N 4 [M+H] + :417.2079,found 417.2070。
example 3
Synthesis of isoindole tetrapyrrole pigment 1 c:
the procedure of example 1 was followed except that the equivalent amount of pyrrole was changed to 2, 4-dimethyl-3-ethylpyrrole (0.12 mL,0.90 mmol), to give 43% of 1c (76 mg).
The nuclear magnetic data and high-resolution mass spectrum data are as follows: 1 H NMR(400MHz,CDCl 3 )δ9.06(d,J＝7.6Hz,2H),8.73(s,2H),7.91(d,J＝7.6Hz,2H),7.51(t,J＝7.3Hz,2H),7.43(t,J＝7.4Hz,2H),2.65(s,6H),2.53(q,J＝7.5Hz,4H),2.38(s,6H),1.16(t,J＝7.5Hz,6H). 13 C NMR(101MHz,CDCl 3 )δ159.8,148.3,141.5,137.8,130.7,128.3,127.5,127.3,126.1,126.1,124.4,122.2,17.7,15.5,12.7,12.0.HRMS(APCI)calcd for C 32 H 33 N 4 [M+H] + :473.2705,found 473.2692。
example 4
Synthesis of isoindole tetrapyrrole pigment 1 d:
the procedure of example 1 was followed except that pyrrole was replaced with N-methylpyrrole (122 mg,1.5 mmol), to give 33% of 1d (48 mg).
The nuclear magnetic data and high-resolution mass spectrum data are as follows: 1 H NMR(300MHz,CDCl 3 )δ8.96(d,J＝7.4Hz,2H),8.03(d,J＝7.3Hz,2H),7.61-7.43(m,4H),7.31(dd,J＝4.1,1.6Hz,2H),7.07(s,2H),6.40(dd,J＝4.1,2.5Hz,2H),4.38(s,6H). 13 C NMR(126MHz,CDCl 3 )δ161.0,148.8,140.6,138.9,131.1,129.2,128.7,128.3,127.1,123.3,117.9,110.2,38.8.HRMS(APCI)calcd for C 26 H 21 N 4 [M+H] + :389.1761,found 389.1757。
example 5
Synthesis of isoindole tetrapyrrole pigment 1 e:
the procedure of example 1 was followed except that pyrrole was changed to N-undecylpyrrole (336 mg,1.5 mmol) to give 1e in 25% yield (39 mg).
The nuclear magnetic data and high-resolution mass spectrum data are as follows: 1 H NMR(300MHz,CDCl 3 )δ8.95(dd,J＝6.0,2.0Hz,2H),8.12-7.96(m,2H),7.58-7.38(m,4H),7.30(s,2H),7.10(s,2H),6.39(dd,J＝4.0,2.5Hz,2H),4.85(t,J＝7.4Hz,4H),2.05-1.86(m,4H),1.40-1.18(m,32H),0.85(t,J＝6.8Hz,6H). 13 C NMR(75MHz,CDCl 3 )δ160.7,148.9,140.5,138.9,129.3,128.2,128.0,127.2,126.6,122.8,117.5,109.5,49.8,32.0,31.8,29.7,29.5,29.5,27.0,22.8,14.3.HRMS(APCI)calcd for C 46 H 61 N 4 [M+H] + :669.4891,found 669.4888。
example 6
Synthesis of isoindole tetrapyrrole pigment 1 f:
the procedure of example 1 was followed, except that pyrrole was changed to 3-methylindole (197mg, 1.5 mmol), to give 11% of 1f (20 mg).
The nuclear magnetic data and high-resolution mass spectrum data are as follows: 1 H NMR(300 MHz,d 6 -DMSO)δ11.57(s,2H),9.07(d,J＝7.2Hz,2H),8.40-8.32(m,2H),7.79–7.59(m,8H),7.33(t,J＝7.6Hz,2H),7.16(t,J＝7.5Hz,2H),2.94(s,6H). 13 C NMR(126MHz,d 6 -DMSO)δ162.5,148.9,139.9,138.5,137.5,129.2,128.9,128.7,126.7,124.9,123.7,120.0,119.9,119.0,112.5,104.5,11.7.HRMS(APCI)calcd for C 34 H 25 N 4 [M+H] + :489.2079,found 489.2073。
detection example 1
The isoindole tetrapyrrole pigments 1a, 1c, 1d and 1e prepared in the above examples were subjected to X-ray single crystal diffraction characterization, and the specific results are shown in FIGS. 1 to 4; FIG. 5 is an absorption spectrum of isoindole tetrapyrrole pigments 1a-f (10. Mu. Mol/L) in methylene chloride; FIG. 6 is an emission spectrum of isoindole tetrapyrrole pigments 1a-f in methylene chloride.
Detection example 2
The basic maximum absorption wavelength, molar absorptivity and maximum emission wavelength of the isoindole tetrapyrrole pigments 1a to f prepared in examples 1 to 6 in methylene chloride and acetonitrile, respectively, are shown in Table 1:
TABLE 1
As can be seen from examples 1-6 above, the present invention provides a process for preparing such tetrapyrrole pigments from isoindolinone and pyrrole and its derivatives by condensing them with phosphorus oxychloride and then dimerizing them in one pot. The raw materials used in the preparation method are commercialized, the raw materials are easy to obtain, the process is simple, and the reaction is efficient. The tetrapyrrole pigment has the advantages of modifiable structure, adjustable spectrum, and large molar absorptivity (up to 70795 cm) -1 ) The maximum absorption wavelength is 510-610nm, the maximum emission spectrum is 580-670nm, and the method has good application prospect in the fields of biomedicine, material science and the like.
The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited to the specific details of the above embodiments, and various simple modifications can be made to the technical solution of the present invention within the scope of the technical concept of the present invention, and all the simple modifications belong to the protection scope of the present invention.
In addition, the specific features described in the above embodiments may be combined in any suitable manner, and the present invention is not limited to the various combinations, unless otherwise specified.
Moreover, any combination of the various embodiments of the invention can be made without departing from the spirit of the invention, which should also be considered as disclosed herein.
Claims (5)
1. A method for preparing isoindole tetrapyrrole pigment, comprising the steps of:
mixing isoindolinone shown in a formula (A), pyrrole shown in a formula (B) or a derivative thereof and a solvent, and performing a first contact reaction under an acidic condition; then, carrying out alkali treatment for second contact reaction;
wherein, the structure of isoindole tetrapyrrole pigment is:
Wherein R1, R2, R3 and R4 are each independently H, C 1 -C 12 Straight or branched alkyl, C 1 -C 12 A linear or branched cycloalkyl group;
the amount of the pyrrole or the derivative thereof is 1.2 to 2mmol relative to 1mmol of isoindolinone;
the conditions of the first contact reaction include: the temperature is 70-150 ℃ and the time is 2-100h;
the alkali treatment comprises alkali extraction and washing which are sequentially carried out, and alkali of the alkali treatment is provided by organic alkali and/or inorganic alkali;
wherein the organic base is triethylamine and/or diethylamine;
the inorganic alkali is one or more of sodium bicarbonate and a solution thereof, potassium bicarbonate and a solution thereof, sodium carbonate and a solution thereof, and potassium carbonate, sodium hydroxide and a solution thereof, and potassium hydroxide and a solution thereof;
the acidic condition is provided by a lewis acid, which is phosphorus oxychloride;
the solvent is one or more of chloroform, 1, 2-methylene dichloride, toluene, chlorobenzene, o-dichlorobenzene, p-dichlorobenzene and m-dichlorobenzene.
2. The preparation method according to claim 1, wherein R1 and R3 are each independently H or methyl;
r2 is each independently H or ethyl;
r4 is each independently H or C 1 -C 12 Straight or branched alkyl of (a).
3. The production method according to claim 1, wherein the conditions of the second contact reaction include: the temperature is 0-120 ℃ and the time is 1-100h.
4. The production method according to claim 1, wherein the pH of the system at the start of the second contact reaction is 7.5 to 14.
5. The production method according to claim 1, wherein the pH of the system at the start of the first contact reaction is 2.0 to 6.0.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911273748.8A CN111057046B (en) | 2019-12-12 | 2019-12-12 | Isoindole tetrapyrrole pigment and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911273748.8A CN111057046B (en) | 2019-12-12 | 2019-12-12 | Isoindole tetrapyrrole pigment and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111057046A CN111057046A (en) | 2020-04-24 |
| CN111057046B true CN111057046B (en) | 2023-06-02 |
Family
ID=70298933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911273748.8A Active CN111057046B (en) | 2019-12-12 | 2019-12-12 | Isoindole tetrapyrrole pigment and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111057046B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105315288A (en) * | 2015-11-24 | 2016-02-10 | 浙江大学 | Method for preparing nafoxidine-pyrazine-isoindole derivative |
| KR20160121282A (en) * | 2015-04-10 | 2016-10-19 | 삼성에스디아이 주식회사 | Compound, organic optoelectric device and display device |
| CN110156660A (en) * | 2019-05-28 | 2019-08-23 | 广东工业大学 | A kind of isoindoline analog derivative and preparation method thereof |
-
2019
- 2019-12-12 CN CN201911273748.8A patent/CN111057046B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160121282A (en) * | 2015-04-10 | 2016-10-19 | 삼성에스디아이 주식회사 | Compound, organic optoelectric device and display device |
| CN105315288A (en) * | 2015-11-24 | 2016-02-10 | 浙江大学 | Method for preparing nafoxidine-pyrazine-isoindole derivative |
| CN110156660A (en) * | 2019-05-28 | 2019-08-23 | 广东工业大学 | A kind of isoindoline analog derivative and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| PI-IOTOCYCLIZATION REACTIONS OF N-SUBSTITUTED THIOPHTHALIMIDES;JOHN D. COYLE 等;《Journal of Photochemistry》;第31卷;387-397 * |
| Red to Near-Infrared Isoindole BODIPY Fluorophores: Synthesis, Crystal Structures, Spectroscopic and Electrochemical Properties;Changjiang Yu 等;《J. Org. Chem.》;1-31 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111057046A (en) | 2020-04-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Saha et al. | Facile and eco-friendly synthesis of chromeno [4, 3-b] pyrrol-4 (1 H)-one derivatives applying magnetically recoverable nano crystalline CuFe 2 O 4 involving a domino three-component reaction in aqueous media | |
| Kour et al. | Iodine–NH 4 OAc mediated regioselective synthesis of 2-aroyl-3-arylimidazo [1, 2-a] pyridines from 1, 3-diaryl-prop-2-en-1-ones | |
| CN107602577A (en) | Chiral bridge ring skeleton hydroxyindole spiro piperidines and its synthetic method | |
| CN106083850B (en) | A kind of pyrimido naphthalimide derivative and its preparation method and application | |
| Yu et al. | Visible-light-irradiated tandem sulfonylation/cyclization of indole tethered alkenes for the synthesis of tetrahydrocarbazoles | |
| JP2004155728A (en) | Method for producing metal complex | |
| CN111057046B (en) | Isoindole tetrapyrrole pigment and preparation method thereof | |
| Chacko et al. | Synthesis of aminomethylphenol derivatives via magnetic nano Fe _ 3 O _ 4 Fe 3 O 4 catalyzed one pot Petasis borono-Mannich reaction | |
| CN102491936A (en) | Conjugated compound with yellow-green fluorescence and preparation method and use thereof | |
| CN112250688A (en) | 7-azabenzofuran derivatives and application thereof in antitumor drugs | |
| CN113845521B (en) | Method for synthesizing imidazo nitrogen-containing heterocyclic hydrazine derivative by aqueous phase photocatalysis one-pot method | |
| CN104710417B (en) | Azaindole derivatives and synthesis method thereof | |
| Biswas et al. | Diastereoselective pot-and atom-economical synthesis of densely-substituted polycyclic 1, 2-and 1, 2, 3-fused indole scaffolds | |
| CN106083649B (en) | A kind of synthetic method of the Cyclohexadiene derivatives of 3,5 diaryl, 2,6,6 tricyano, 1 imino group 2,4 | |
| CN111057390B (en) | Linear conjugated isoindole polypyrrole pigment and preparation method thereof | |
| Peng et al. | Simultaneous enhancement of fluorescence and solubility by N-alkylation and functionalization of 2-(2-thienyl) imidazo [4, 5-f][1, 10]-phenanthroline with heterocyclic bridges | |
| CN109369772B (en) | Synthetic method and anti-tumor application of phenanthridine nitidine derivatives | |
| CN110078749B (en) | 3a, 3a' -difuran [2,3-b ] indoline compound, preparation method, pharmaceutical composition and application | |
| CN113072470A (en) | N-acetonitrile bis-benzenesulfonylimine derivative and preparation method and application thereof | |
| CN108484595B (en) | Simple synthesis method of asthma medicine Fevipiprant | |
| CN111333670B (en) | Isoindole fluorine boron tripyrrole fluorescent dye and preparation method thereof | |
| CN109369658B (en) | Synthesis method of spiro [ pyrrolidine-3, 3' -oxindole ] ring systems | |
| CN103058988B (en) | Thionaphthene and derivative and preparation method thereof thereof and application | |
| CN113620859B (en) | Method for synthesizing indeno [2,1-b ] indol-6 (5H) -one derivative | |
| CN106866706A (en) | A kind of synthetic method of benzo [d] pyrrolo- [2,1 b] thiazole |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |