CN108727413A - A kind of thiazole bioxindol class compound and preparation method thereof - Google Patents

A kind of thiazole bioxindol class compound and preparation method thereof Download PDF

Info

Publication number
CN108727413A
CN108727413A CN201710238042.2A CN201710238042A CN108727413A CN 108727413 A CN108727413 A CN 108727413A CN 201710238042 A CN201710238042 A CN 201710238042A CN 108727413 A CN108727413 A CN 108727413A
Authority
CN
China
Prior art keywords
compound
preparation
thiazole
thiazoleaminos
pyrrolo
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.)
Pending
Application number
CN201710238042.2A
Other languages
Chinese (zh)
Inventor
万晓波
张焕瑞
李晨晨
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Qingdao Institute of Bioenergy and Bioprocess Technology of CAS
Original Assignee
Qingdao Institute of Bioenergy and Bioprocess Technology of CAS
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Qingdao Institute of Bioenergy and Bioprocess Technology of CAS filed Critical Qingdao Institute of Bioenergy and Bioprocess Technology of CAS
Priority to CN201710238042.2A priority Critical patent/CN108727413A/en
Publication of CN108727413A publication Critical patent/CN108727413A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

The present invention relates to a kind of thiazole bioxindol class compounds and preparation method thereof.The general structure of the thiazole bioxindol class compound is such as（I）Shown, preparation method is using 4- thiazoles amino acid salt as raw material, by series of steps such as acylation, alkylation, hydrolysis, chlorination, cyclisation, has successfully obtained thiazole bioxindol class compound shown in structural formula I.The compound of the present invention can have good application prospect as important receptor unit in organic photoelectrical material field.

Description

A kind of thiazole bioxindol class compound and preparation method thereof
Technical field
The present invention relates to a kind of thiazole bioxindol class compound and preparation method thereof, belong to heterocyclic compound synthesis and organic Field of semiconductor materials.
Background technology
Bioxindol class formation has good coplanarity, the preferable pi-pi accumulation of easy formation and good environmental stability, makees It is widely used in the field of photoelectric devices such as organic field effect tube, organic solar batteries for important receptor unit （Adv. Mater, 2016,28,3615-3645；Chem. Mater., 2016, 28, 1286-1297; Acc. Chem. Res., 2014, 47, 1117-1126）.Therefore, the design of the bioxindol compound based on new construction has with synthesis There is important researching value.Thiazole bioxindol structure has coplanarity good, the low easily prepared n- semi-conducting materials of energy level The advantages that, up to the present have no document report.The small molecule of design and synthetizing thiazolium bioxindol class compound and its structure and Polymer will be with important research significance and application value in organic photoelectric field.
In conclusion bioxindol class compound is widely used in field of photovoltaic materials, the bioxindol chemical combination based on new construction The design of object has important researching value with synthesis.Currently, thiazole bioxindol class compound has not been reported in the literature, carry out There is important research significance and application in organic photoelectrical material field based on the design of thiazole bioxindol class formation and synthetic work Value.
Invention content
It is an object of the present invention to provide a kind of thiazole bioxindol class compounds and preparation method thereof.
Specifically, the general structure of the thiazole bioxindol class compound is such as（Ⅰ）It is shown：
（Ⅰ）
Wherein：
R is C31 alkyl below, C31 acyl groups below, C18 aryl below, C18 heteroaryls below；X is derived from Br, Cl, I, TfO, MsO.
The invention discloses a kind of preparation method of thiazole bioxindol class compound, the chemical name of the compound be (E)- [bis- pyrrolo- [3,2- of 6,6'-b] thiazole subunit] -5,5'(4H,4'H)-diketone, preparation method is to be original with 4- thiazole amino acid salts Material, by series of steps such as acylation, alkylation, hydrolysis, halogenation and cyclisation, has successfully obtained targeted shown in structural formula I Close object.
The present invention disclose preparation (E)-[bis- pyrrolo- [3,2- of 6,6'-b] thiazole subunit] -5,5'(4H,4'H)-diketone The method of class compound includes the following steps：
（1）Using 4- thiazoles amino acid salt as starting material, ammonolysis reaction occurs with acetyl halide compound and prepares 2,
Wherein, oxalic acid mono ethyl ester carboxylic acid halides is oxalic acid mono ethyl ester acyl chlorides or oxalic acid mono ethyl ester acylbromide；R1For C18 alkyl below, virtue Base；
（2）2, which occur alkylated reaction, prepares 3
（3）3 generation macromolecule alkali for hydrolysis obtain 4,
（4）4 generate 5 through halogenation, cyclization,
（5）5 react generation target compound 6 with Lawesson reagents.
The preparation 2-（4- thiazoleaminos）- 2- oxoacetate esters（Compound 2）Carboxylic acid halides used is selected from oxalic acid list second Ester carboxylic acid halides is oxalic acid mono ethyl ester acyl chlorides or oxalic acid mono ethyl ester acylbromide, R1Selected from C18 alkyl below, aryl；The preparation 2-（N- Substitution -4- thiazoleaminos）- 2- oxoacetate esters（Compound 3）Alkylating reagent used be selected from brominated alkanes, chloralkane, Alkane iodide, alkyl sulfonic ester, alkyl phosphate, aryl bromide, chlorinated aromatic hydrocarbons, iodo aromatic hydrocarbon, aromatic yl sulphonate, aryl phosphoric acids One or more of mixtures of ester；The preparation 2-（NSubstitution -4- thiazoleaminos）- 2- Oxoacetic Acids（Compound 4）Institute Alkali be selected from lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, barium hydroxide, potassium phosphate, sodium phosphate one kind or Several mixtures；The preparation 4- substitutions -4HPyrrolo- [2,3-d] thiazole -5,6- diketone（Compound 5）Halogen used Change reagent and is selected from oxalyl chloride, oxalyl bromine, thionyl chloride, boron chloride, phosphorus trichloride, Boron tribromide, phosphorus tribromide, phosphoric The mixture of the one or more such as phosphorus, phosphorus pentabromide；Cyclization reagent used in it is selected from lithium diisopropylamine, 2,2,6,6- tetra- The mixture of the one or more such as methyl piperidine lithium, hexamethl disilamine lithium, hexamethl disilamine potassium；The preparation (E)- [bis- pyrrolo- [2,3- of 6,6'-d] thiazole subunit] -5,5'(4H,4'H)-diketone（Compound 6）Reagent used is selected from Lawesson reagents.
The preparation 2-（4- thiazoleaminos）- 2- oxoacetate esters（Compound 2）Solvent used be selected from tetrahydrofuran, Dioxane, glycol dimethyl ether, dimethyl sulfoxide (DMSO), dichloromethane, 1,2- dichloroethanes, chloroform, carbon tetrachloride one kind or Several mixtures；The preparation 2-（NSubstitution -4- thiazoleaminos）- 2- oxoacetate esters（Compound 3）Solvent choosing used From tetrahydrofuran, dioxane, glycol dimethyl ether, dimethyl sulfoxide (DMSO),N,NDimethylformamide,N,NDimethylacetylamide One or more of mixtures；The preparation 2-（NSubstitution -4- thiazoleaminos）- 2- Oxoacetic Acids（Compound 4）It is used Solvent be selected from tetrahydrofuran, water, glycol dimethyl ether, dimethyl sulfoxide (DMSO), ethyl alcohol, methanol, isopropanol it is one or more of Mixture；The preparation 4- substitutions -4HPyrrolo- [2,3-d] thiazole -5,6- diketone（Compound 5）Solvent used is selected from One or more of mixtures of tetrahydrofuran, dioxane, glycol dimethyl ether, dimethyl sulfoxide (DMSO), toluene；The preparation (E)[bis- pyrrolo- [2,3- of 6,6'-d] thiazole subunit] -5,5'(4H,4'H)-diketone（Compound 6）Solvent used is selected from Benzene, toluene, ortho-xylene, meta-xylene, paraxylene tetrahydrofuran, dioxane, glycol dimethyl ether,N,NDimethyl methyl One or more of mixtures of amide, dimethyl sulfoxide (DMSO), dichloromethane, 1,2- dichloroethanes, chloroform, carbon tetrachloride, acetonitrile.
The preparation 2-（4- thiazoleaminos）- 2- oxoacetate esters（Compound 2）Reaction temperature be 0oC- solvents Reflux temperature；The preparation 2-（NSubstitution -4- thiazoleaminos）- 2- oxoacetate esters（Compound 3）Reaction temperature be 0oC- The reflux temperature of solvent；The preparation 2-（NSubstitution -4- thiazoleaminos）- 2- Oxoacetic Acids（Compound 4）Reaction temperature It is 0oThe reflux temperature of C- solvents；The preparation 4- substitutions -4HPyrrolo- [2,3-d] thiazole -5,6- diketone（Compound 5） Reaction temperature be -80oC- room temperatures.The preparation (E)-[bis- pyrrolo- [2,3- of 6,6'-d] thiazole subunit] -5,5'(4H, 4'H)-diketone（Compound 6）Reaction temperature used is 0oThe reflux temperature of C- solvents.
Present invention provides a kind of thiazole isatin class compounds and preparation method thereof.
Specifically, the general structure of the thiazole isatin class compound is such as（III）It is shown：
（III）
Wherein：
R is C31 alkyl below, C31 acyl groups below, C18 aryl below, C18 heteroaryls below；X is derived from Br, Cl, I, TfO, MsO.
The present invention is 4HThiazole simultaneously [3,2-b] pyrroles -5,6- diketone and (E)-[bis- pyrrolo- [3,2- of 6,6'-b] thiazole Subunit] -5,5'(4H,4'HThe novel processing step of)-cyclohexadione compounds, synthesis material are easy to get, and post-processing is easy.The present invention Reaction route is novel, and product is all noval chemical compound, has no document report.
Table 1-2 lists the 4 of the present inventionHThiazole simultaneously [3,2-b] pyrroles -5,6- diketone and (E)-[bis- pyrrolo-es of 6,6'- [3,2-b] thiazole subunit] -5,5'- (4H,4'HThe concrete structure of)-cyclohexadione compounds substituent group, but the present invention is not limited to These compounds.
Table 1
1 general structure of table（I,II）Compound represented structure
2 general structure of table（I,II）Compound represented structure
Specific implementation mode
With reference to the example in detail present invention, but following experiment embodiment is only the preferable embodiment party of the present invention Formula, scope of protection of the present invention is not limited thereto, skill of any one skilled in the art in present disclosure Within the scope of art, it is subject to equivalent substitution or change according to the technical scheme of the invention and its inventive conception, should all covers in the present invention Protection domain within.
Embodiment 1
Prepare 2-（The bromo- 4- thiazoleaminos of 2-）- 2- ethyls（Compound 2a）
At room temperature, into the tube sealing of 100 mL, the bromo- 4- thiazoles amine hydrobromates of 2- are added（7.74 g, 30 mmol), 60 mL Dry tetrahydrofuran dissolving, is added ethyl oxalyl chloride（4.51 g, 33 mmol, 1.1 eq.）.Reaction in oil bath 100oC reacts 2 h.It is extracted with ethyl acetate, then massive laundering is washed with saturated sodium bicarbonate aqueous solution, anhydrous Na SO4It is dry. It is concentrated to obtain compound 2a crude products, through column chromatography（Petrol ether/ethyl acetate）Detach compound 2a be 5.86 g of white solid, Yield 70%.
1H NMR (600 MHz, CDCl3) δ 9.60 (2s, 1H), 7.70 (2s, 1H), 4.43 (q, J = 7.2 Hz, 2H), 1.43 (t, J = 7.2 Hz, 3H); 13C NMR (151 MHz, CDCl3) δ 159.55, 159.51, 153.64, 153.57, 151.17, 145.12, 143.64, 135.29, 107.65, 105.73, 63.93, 13.99.
Prepare 2-（NDodecyl -4- thiazoleaminos）- 2- ethyls（Compound 3a）
Under argon atmospher, into the reaction bulb of 100 mL, compound 2a crude products are added（5.58 g, 20 mmol), 40% K2CO3- Al2O3（20.73 g, 60 mmol, 3eq.）And bromododecane（7.48 g, 30 mmol, 1.5 eq.), with 50 mL Dry DMF dissolvings, are heated to 100oC reacts 2 h.After reaction is cooling, saturation NH is added4The quenching reaction of Cl solution.Use acetic acid Ethyl ester extracts, washing, saturated common salt water washing, anhydrous Na SO4It is dry.Organic phase concentrates, column chromatography（Eluant, eluent is PE:EA= 30）Detach to obtain 3a containing compound（NAlkylation）AndOThe mixture of alkylate, 6.71 g of faint yellow solid, yield 75%. Wherein 3a：OAlkylate=4:1.
3a：OAlkylate=4:1；The nuclear magnetic data of mixture：1H NMR (600 MHz, CDCl3) for N- alkylated isomer: δ 6.88 (s, 1H), 4.20 (q, J = 7.1 Hz, 2H), 3.85-3.76 (m, 2H), 1.64-1.56 (m, 2H), 1.37-1.12 (m, 21H), 0.88 (t, J = 7.1 Hz, 3H); 1H NMR (600 MHz, CDCl3) for O-alkylated isomers: δ 7.72 (s, 1H), 4.40 (q, J = 7.1 Hz, 2H), 3.94-3.85 (m, 2H), 1.74-1.65 (m, 2H), 1.40 (t, J = 7.1 Hz, 3H), 1.38-1.15 (m, 18H), 0.88 (t, J = 7.1 Hz, 3H); 13C NMR (151 MHz, CDCl3) for all the isomer: δ 162.24, 162.09, 161.07, 151.44, 149.32, 147.89, 145.49, 135.46, 113.04, 111.82, 111.35, 109.86, 62.40, 62.07, 48.81, 47.03, 46.96, 31.90, 29.60, 29.53, 29.44, 29.33, 29.20, 29.16, 29.06, 27.31, 26.61, 26.45, 25.93, 22.67, 14.11, 13.98, 13.88, 13.84.
Prepare 2-（NDodecyl -4- thiazoleaminos）- 2- Oxoacetic Acids（Compound 4a）
Compound 3a is added into the reaction tube of 100ml（8.95 g, 20 mmol), 1 M LiOH are added dropwise after ice bath cooling（60 Ml, 3 eq.）.After being added dropwise, saturation NH is added4The quenching reaction of Cl solution.It is extracted with ethyl acetate, washes, saturated salt solution Washing, anhydrous Na SO4It is dry.Organic phase is concentrated to give the compound 4a crude products containing o-alkylation product, yield 89%.4a crude products Without purification, it is directly used in and reacts in next step.
Prepare 4- dodecyls -4HPyrrolo- [2,3-d] thiazole -5,6- diketone（Compound 5a）
Under argon atmospher, into the reaction bulb of 50 mL, compound 4a is added（0.84 g, 2 mmol), dry tetrahydrofuran dissolving, Ice bath cools down, and SOCl is then added dropwise2（144 μ L, 2 mmol, 1.0 eq.）, ice bath is withdrawn, 2 h are reacted at room temperature.It then will be anti- Liquid is answered to move to cooling in ethyl acetate-liquid nitrogen bath.0.5 M 2,2,6,6- tetramethyl piperidines lithium-first is slowly added dropwise into reaction solution Benzole soln（Abbreviation LTMP, 8 ml, 2.0 eq.）.0.5 h of rear low-temp reaction is added dropwise.Saturation NH is added4The quenching of Cl solution is anti- It answers.It is extracted with ethyl acetate, washes, saturated common salt water washing, anhydrous Na SO4It is dry.Organic phase concentrates, through rapid column chromatography point From compound 5a, 0.24 g of rufous liquid, yield 30%.
1H NMR (600 MHz, CDCl3) δ 3.76-3.74 (m, 2H), 1.74-1.71 (m, 2H), 1.33- 1.25 (m, 18H), 0.88 (t, J = 7.0 Hz, 3H); 13C NMR (151 MHz, CDCl3) δ 174.57, 170.86, 170.16, 160.00, 102.30, 41.89, 32.11, 29.81, 29.73, 29.66, 29.54, 29.27, 28.41, 26.84, 22.90, 14.39.
Prepare (E) -4,4 '-dodecyl-[bis- pyrrolo- [2,3- of 6,6'-d] thiazole subunit] -5,5'(4H,4'H)-diketone（Change Close object 6a）
Under argon atmospher, into the reaction bulb of 50 mL, compound 5a is added（0.20 g, 0.5 mmol), dry toluene dissolving adds Enter Lawesson reagents（0.10 g, 0.25 mmol, 0.5 eq.), it is heated to 60oC reacts 30 min.After reaction is cooling, Organic phase concentrates, and 0.17 g of compound 5a blue solids, yield 45% are obtained through column chromatography for separation.
1H NMR (600 MHz, CDCl3) δ 3.85-3.83 (m, 4H), 1.77-1.75 (m, 4H), 1.33 - 1.25 (m, 36H), 0.88 (t, J = 7.0 Hz, 6H); 13C NMR (151 MHz, CDCl3) δ 168.99, 160.92, 159.36, 119.28, 106.10, 77.23, 77.02, 76.81, 41.36, 31.93, 29.63, 29.55, 29.49, 29.35, 29.14, 28.48, 26.72, 22.70, 14.13.

Claims (7)

1. a kind of thiazole bioxindol class compound and preparation method thereof, the general structure of the thiazole bioxindol class compound is such as （Ⅰ）It is shown：
（Ⅰ）
It is characterized in that, R is C31 alkyl below, and C31 acyl groups below, C18 aryl below, C18 heteroaryls below；X It is derived from Br, Cl, I, TfO, MsO.
2. the synthesis of thiazole bioxindol class compound is as follows：It is characterized in that, using 4- thiazoles amino acid salt as raw material, by acylation, The series of steps such as alkylation, hydrolysis, halogenation and cyclisation successfully synthesize target compound I, and specific synthetic method is by following Route（II）It carries out, which uses conventional organic synthesis,
（II）.
3. according to method shown in claim 2, it is characterized in that five step reaction is,
（1）Using 4- thiazoles amino acid salt as starting material, ammonolysis reaction occurs with acetyl halide compound and prepares 2,
Wherein, oxalic acid mono ethyl ester carboxylic acid halides is oxalic acid mono ethyl ester acyl chlorides or oxalic acid mono ethyl ester acylbromide；R1For C18 alkyl below, virtue Base；
（2）2, which occur alkylated reaction, prepares 3
（3）3 generation macromolecule alkali for hydrolysis obtain 4,
（4）4 generate 5 through halogenation, cyclization,
（5）5 react generation target compound 6 with Lawesson reagents,
。
4. according to the method for claim 2-3, which is characterized in that the preparation 2-（4- thiazoleaminos）- 2- oxoacetate esters （Compound 2）It is oxalic acid mono ethyl ester acyl chlorides or oxalic acid mono ethyl ester acylbromide, R that carboxylic acid halides used, which is selected from oxalic acid mono ethyl ester carboxylic acid halides,1It is selected from C18 alkyl below, aryl；The preparation 2-（NSubstitution -4- thiazoleaminos）- 2- oxoacetate esters（Compound 3）Used Alkylating reagent is selected from brominated alkanes, chloralkane, alkane iodide, alkyl sulfonic ester, alkyl phosphate, aryl bromide, chloro Aromatic hydrocarbons, iodo aromatic hydrocarbon, aromatic yl sulphonate, one or more of mixtures of aryl phosphate ester；The preparation 2-（NSubstitution- 4- thiazoleaminos）- 2- Oxoacetic Acids（Compound 4）Alkali used is selected from lithium hydroxide, sodium hydroxide, potassium hydroxide, hydroxide One or more of mixtures of caesium, barium hydroxide, potassium phosphate, sodium phosphate；The preparation 4HPyrrolo- [2,3-d] thiazole- 5,6- cyclohexadione compounds（Compound 5）Halide reagent used is selected from oxalyl chloride, oxalyl bromine, thionyl chloride, boron chloride, three The mixture of the one or more such as phosphorus chloride, Boron tribromide, phosphorus tribromide, phosphorus pentachloride, phosphorus pentabromide；Cyclisation examination used in it Agent is selected from the one kind such as lithium diisopropylamine, 2,2,6,6- tetramethyl piperidines lithium, hexamethl disilamine lithium, hexamethl disilamine potassium Or several mixture；The preparation (E)-[bis- pyrrolo- [2,3- of 6,6'-d] thiazole subunit] -5,5'(4H,4'H)-diketone Class compound（Compound 6）Reagent used is selected from Lawesson reagents.
5. according to the method for claim 2-3, which is characterized in that the preparation 2-（4- thiazoleaminos）- 2- oxoacetate esters （Compound 2）Solvent used is selected from tetrahydrofuran, dioxane, glycol dimethyl ether, dimethyl sulfoxide (DMSO), dichloromethane, 1, One or more of mixtures of 2- dichloroethanes, chloroform, carbon tetrachloride；The preparation 2-（NSubstitution -4- thiazoleaminos）-2- Oxoacetate ester（Compound 3）Solvent used be selected from tetrahydrofuran, dioxane, glycol dimethyl ether, dimethyl sulfoxide (DMSO),N,NDimethylformamide,N,NOne or more of mixtures of dimethylacetylamide；The preparation 2-（NSubstitution -4- thiophenes Azoles amino）- 2- Oxoacetic Acids（Compound 4）Solvent used be selected from tetrahydrofuran, water, glycol dimethyl ether, dimethyl sulfoxide (DMSO), One or more of mixtures of ethyl alcohol, methanol, isopropanol；The preparation 4HPyrrolo- [2,3-d] thiazole -5,6- diketone Class compound（Compound 5）Solvent used is selected from tetrahydrofuran, dioxane, glycol dimethyl ether, dimethyl sulfoxide (DMSO), toluene One or more of mixtures；The preparation (E)[bis- pyrrolo- [2,3- of 6,6'-d] thiazole subunit] -5,5'(4H,4'H)-cyclohexadione compounds（Compound 6）Solvent used is selected from benzene, toluene, ortho-xylene, meta-xylene, paraxylene tetrahydrochysene Furans, dioxane, glycol dimethyl ether,N,NDimethylformamide, dimethyl sulfoxide (DMSO), dichloromethane, 1,2- dichloroethanes, One or more of mixtures of chloroform, carbon tetrachloride, acetonitrile.
6. according to the method for claim 2-3, which is characterized in that the preparation 2-（4- thiazoleaminos）- 2- oxoacetate esters （Compound 2）Reaction temperature be 0oThe reflux temperature of C- solvents；The preparation 2-（NSubstitution -4- thiazoleaminos）- 2- oxos Acetic acid esters（Compound 3）Reaction temperature be 0oThe reflux temperature of C- solvents；The preparation 2-（NSubstitution -4- thiazole ammonia Base）- 2- Oxoacetic Acids（Compound 4）Reaction temperature be 0oThe reflux temperature of C- solvents；The preparation 4HPyrrolo- [2, 3-d] thiazole -5,6- cyclohexadione compounds（Compound 5）Reaction temperature be -80oC- room temperatures；The preparation (E)-[6, Bis- pyrrolo- [2,3- of 6'-d] thiazole subunit] -5,5'(4H,4'H)-cyclohexadione compounds（Compound 6）Reaction temperature used It is 0oThe reflux temperature of C- solvents.
7. such as according to the general structure of claim 2-3 compounds represented 5（III）It is shown：
（III）
It is characterized in that, R is C31 alkyl below, and C31 acyl groups below, C18 aryl below, C18 heteroaryls below；X It is derived from Br, Cl, I, TfO, MsO.
CN201710238042.2A 2017-04-13 2017-04-13 A kind of thiazole bioxindol class compound and preparation method thereof Pending CN108727413A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201710238042.2A CN108727413A (en) 2017-04-13 2017-04-13 A kind of thiazole bioxindol class compound and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201710238042.2A CN108727413A (en) 2017-04-13 2017-04-13 A kind of thiazole bioxindol class compound and preparation method thereof

Publications (1)

Publication Number Publication Date
CN108727413A true CN108727413A (en) 2018-11-02

Family

ID=63923678

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201710238042.2A Pending CN108727413A (en) 2017-04-13 2017-04-13 A kind of thiazole bioxindol class compound and preparation method thereof

Country Status (1)

Country Link
CN (1) CN108727413A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114618587A (en) * 2020-12-09 2022-06-14 万华化学集团股份有限公司 Vanadium ligand catalyst, preparation method and application thereof in phenol hydroxylation reaction

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101486721A (en) * 2009-02-17 2009-07-22 浙江联盛化学工业有限公司 Use of lithium diisopropyl amido in 1-methyl cyclopropene preparation
US20100160323A1 (en) * 2008-12-23 2010-06-24 Alexander Bischoff NOVEL PIPERAZINE DERIVATIVES AS INHIBITORS OF STEAROYL-CoA DESATURASE
JP2012109365A (en) * 2010-11-17 2012-06-07 Konica Minolta Holdings Inc Organic photoelectric conversion element and solar cell
KR20140101978A (en) * 2013-02-13 2014-08-21 부산대학교 산학협력단 organic semiconductor compound, manufacturing method thereof, and organic electronic device that contains it

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100160323A1 (en) * 2008-12-23 2010-06-24 Alexander Bischoff NOVEL PIPERAZINE DERIVATIVES AS INHIBITORS OF STEAROYL-CoA DESATURASE
CN101486721A (en) * 2009-02-17 2009-07-22 浙江联盛化学工业有限公司 Use of lithium diisopropyl amido in 1-methyl cyclopropene preparation
JP2012109365A (en) * 2010-11-17 2012-06-07 Konica Minolta Holdings Inc Organic photoelectric conversion element and solar cell
KR20140101978A (en) * 2013-02-13 2014-08-21 부산대학교 산학협력단 organic semiconductor compound, manufacturing method thereof, and organic electronic device that contains it

Non-Patent Citations (18)

* Cited by examiner, † Cited by third party
Title
ASHRAF, RAJA SHAHID等: "A new thiophene substituted isoindigo based copolymer for high performance", 《CHEMICAL COMMUNICATIONS》 *
CHEN, CHI-MIN等: "Thienoisoindigo-based copolymer with fused thieno[3,2-b]thiophene as a donor in thin film transistor applications with high performance", 《JOURNAL OF MATERIALS CHEMISTRY C: MATERIALS FOR OPTICAL AND ELECTRONIC DEVICES》 *
CHEN, MARK S.等: "Control of Polymer-Packing Orientation in Thin Films through Synthetic Tailoring of Backbone Coplanarity", 《CHEMISTRY OF MATERIALS》 *
DUTTA, GITISH K.等: "Visible-Near Infrared Absorbing Polymers Containing Thienoisoindigo and Electron-Rich Units for Organic Transistors with Tunable Polarity", 《ADVANCED FUNCTIONAL MATERIALS》 *
GIJS W. P. VAN PRUISSEN,等: "Synthesis and properties of small band gap thienoisoindigo based conjugated polymers", 《JOURNAL OF DYNAMIC ARTICLE LINKSC<MATERIALS CHEMISTRY》 *
GYOUNGSIK KIM等: "A Thienoisoindigo-Naphthalene Polymer with Ultrahigh Mobility of 14.4 cm2/V•s That Substantially Exceeds Benchmark Values for Amorphous Silicon Semiconductors", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 *
HAILONG ZHAO等: "Synthesis and Pin1 inhibitory activity of thiazole derivatives", 《BIOORGANIC & MEDICINAL CHEMISTRY》 *
HASEGAWA, TSUKASA等: "An ultra-narrow bandgap derived from thienoisoindigo polymers: structural influence on reducing the bandgap and self-organization", 《AN ULTRA-NARROW BANDGAP DERIVED FROM THIENOISOINDIGO POLYMERS: STRUCTURAL INFLUENCE ON REDUCING THE BANDGAP AND SELF-ORGANIZATION》 *
HENRIK SUNE ANDERSEN等: "Discovery and SAR of a Novel Selective and Orally Bioavailable Nonpeptide Classical Competitive Inhibitor Class of Protein-Tyrosine Phosphatase 1B", 《J. MED. CHEM.》 *
HUANG, JING等: "Thienoisoindigo-based small molecules and narrow bandgap polymers synthesized via C-H direct arylation coupling", 《JOURNAL OF POLYMER SCIENCE, PART A: POLYMER CHEMISTRY》 *
JINFENG HAN等: "Low-bandgap donor–acceptor polymers for photodetectors with photoresponsivity from 300 nm to 1600 nm", 《MATERIALS CHEMISTRY C: MATERIALS FOR OPTICAL AND ELECTRONIC DEVICES》 *
KARAKAWA, MAKOTO 等: "Near-Infrared Photovoltaic Performance of Conjugated Polymers Containing", 《MACROMOLECULAR CHEMISTRY AND PHYSICS》 *
MASON, JEFFREY J.;: "A New Approach to Methoxyisatins Leading to the Total Synthesis of Ophiuroidine", 《CHEMINFORM》 *
QI, JI等: "Optimization of Broad-Response and High-Detectivity Polymer Photodetectorsby Bandgap Engineering of Weak Donor-Strong Acceptor Polymers", 《MACROMOLECULES》 *
RICHARD M. SOIL等: "Multigram Preparation of l,8-Diethyl-7-hydroxy-l,3,4,9-tetrahydropyrano-[3,4-6 ]indole- 1-acetic Acid, a Phenolic Metabolite of the Analgesic and Antiinflammatory Agent Etodolac", 《J. ORG. CHEM.》 *
YOO, DONGHO等: "N-Unsubstituted thienoisoindigos: preparation, molecular packing and ambipolar organic field-effect transistors", 《MATERIALS CHEMISTRY C: MATERIALS FOR OPTICAL AND ELECTRONIC DEVICES》 *
YOU, LIYAN等: "Direct arylation polymerization of asymmetric push-pull aryl halides", 《POLYMER CHEMISTRY》 *
YUN, HUI-JUN等: "Polarity Engineering of Conjugated Polymers by Variation of Chemical Linkages Connecting Conjugated Backbones", 《ACS APPLIED MATERIALS & INTERFACES》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114618587A (en) * 2020-12-09 2022-06-14 万华化学集团股份有限公司 Vanadium ligand catalyst, preparation method and application thereof in phenol hydroxylation reaction
CN114618587B (en) * 2020-12-09 2023-10-20 万华化学集团股份有限公司 Vanadium ligand catalyst, preparation method and application thereof in phenol hydroxylation reaction

Similar Documents

Publication Publication Date Title
TW201602101A (en) Method for producing fused heterocyclic compound
KR101501856B1 (en) Novel processes for the manufacture of propane-1-sulfonic acid｛3-[5-(4-chloro-phenyl)-1h-pyrrolo[2,3-b]pyridine-3-carbonyl]-2,4-difluoro-phenyl｝-amide
CA2553311A1 (en) Improved process for the preparation of biologically active tetrahydrobenzthiazole derivative
CN108727413A (en) A kind of thiazole bioxindol class compound and preparation method thereof
CN110372463B (en) Method for synthesizing sulfonamide compound by coupling of nitroaromatic and boric acid compound
JP6256484B2 (en) Method for producing pyridazine compound
WO2010097802A2 (en) A process for the preparation of etoricoxib
Hascall et al. Synthesis and Structural Characterization of [{(Et2O) Mg} 6 (NPh) 4Br4]: A Magnesium–Imide Cage Species Derived from a Dimagnesylamine Solution
JP6909096B2 (en) Method for forming catalyst, amide bond, and method for producing amide compound
BR112021011084A2 (en) PROCESS FOR PREPARING 1-[(3R,4S)-4-CYANOTETRAHYDROPYRAN-3-IL]-3-[(2-FLUORO-6-METOXY-4-PYRIDYL)AMINO]PYRAZOLE-4-CARBOXAMIDE
CN113121401A (en) N-substituted carbonyl fluorosulfonamide compound, preparation method and application thereof
Mori et al. Formation of Seven-Membered-Ring Fused Bithiophene Derivatives by Nosyl Annulation
CN108727414A (en) A kind of unsubstituted thiophene bioxindol class compounds of N- and preparation method thereof
Potter et al. A synthetic entry into the 2‐and 3‐substituted‐methyl 2, 3‐dihydro‐1, 4‐benzoxazine series
WO2017209458A1 (en) Novel method for preparing 4&#39;-hydroxy-4-biphenylcarboxylic acid
PL69905B1 (en)
SE455502B (en) PROCEDURE FOR DEACYLATION OF 1-ACYL-2-IMIDAZOLINE
JP2014151285A (en) New optically active imidazoline-phosphoric acid catalyst and derivative thereof
RU2804686C2 (en) SYNTHESIS OF 3-METHYL-1,2,4-THIADIAZOLE-5-CARBOHYDRAZIDE OR ITS METHYL-d3 DUTERATED FORM
CN113880755B (en) Preparation method of 2-bromo-5- (trifluoromethoxy) pyridine
CN112441984B (en) Benzimidazole-substituted phenyl n-butyramide-based compound and preparation method thereof
HU192070B (en) Process for transforming carboxy group into trichloro-methyl group
RU2575478C2 (en) NOVEL METHODS OF PRODUCING PROPANE-1-SULPHONIC ACID {3-[5-(4-CHLORO-PHENYL)-1H-PYRROLO[2,3-b]PYRIDINE-3-CARBONYL]-2,4-DIFLUORO-PHENYL}-AMIDE
JP2022546126A (en) Benzimidazole-substituted phenyl-n-butanamide compound and method for producing same
CN108424410A (en) A kind of preparation method of rizatriptan

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
WD01 Invention patent application deemed withdrawn after publication
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20181102