PL217059B1 - Compounds, derivatives of 12-phenyl-12H-quinoxaline-[2,3-b] [1,4] benzothiazine and the process for their preparation - Google Patents
Compounds, derivatives of 12-phenyl-12H-quinoxaline-[2,3-b] [1,4] benzothiazine and the process for their preparationInfo
- Publication number
- PL217059B1 PL217059B1 PL398084A PL39808412A PL217059B1 PL 217059 B1 PL217059 B1 PL 217059B1 PL 398084 A PL398084 A PL 398084A PL 39808412 A PL39808412 A PL 39808412A PL 217059 B1 PL217059 B1 PL 217059B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- compounds
- compound
- iodobenzene
- phenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 21
- FBOSKQVOIHEWAX-UHFFFAOYSA-N benzothiazine Chemical compound C1=CC=C2N=CCSC2=C1 FBOSKQVOIHEWAX-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 claims description 10
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 230000005713 exacerbation Effects 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- OYKPJMYWPYIXGG-UHFFFAOYSA-N 2,2-dimethylbutane;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.CCC(C)(C)C OYKPJMYWPYIXGG-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- PHGDRJZYOQJYIJ-UHFFFAOYSA-N 12-phenylquinoxalino[2,3-b][1,4]benzothiazine Chemical class C1(=CC=CC=C1)N1C2=C(SC3=C1C=CC=C3)N=C1C=CC=CC1=N2 PHGDRJZYOQJYIJ-UHFFFAOYSA-N 0.000 description 1
- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical class C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Description
Przedmiotem wynalazku są związki, pochodne 12-fenylo-12H-chinoksalino-[2,3-b][1,4]-benzotiazyny oraz sposób ich wytwarzania.The present invention relates to 12-phenyl-12H-quinoxaline- [2,3-b] [1,4] -benzothiazine compounds and their preparation.
Z opisów zgłoszeń patentowych nr US 2005/0 095 519 A1 oraz nr US 2009/0 026 928 A1 znane są N-fenylopodstawione pochodne fenotiazyny o wzorze A:N-phenyl substituted phenothiazine derivatives of the formula A are known from the specifications of the patent applications No. US 2005/0 095 519 A1 and No. US 2009/0 026 928 A1:
X wzór A w którym X oznacza atom wodoru lub grupę alkilową. Związki te otrzymuje się w wyniku reakcji fenotiazyny z bromoalkilobenzenem w obecności związku palladu oraz tritertbutylofosfmy, w toluenie w temperaturze 80°C lub w wyniku reakcji fenotiazyny ze związkiem jodoaromatycznym w obecności miedzi, bezwodnego węglanu potasu oraz eteru koronowego, w dichlorobenzenie.X is the formula A wherein X is a hydrogen atom or an alkyl group. These compounds are obtained by reacting phenothiazine with bromoalkylbenzene in the presence of a palladium compound and tritert-butylphosphine in toluene at 80 ° C or by reacting phenothiazine with an iodoaromatic compound in the presence of copper, anhydrous potassium carbonate and crown ether in dichlorobenzene.
Wynalazek dotyczy związków, pochodnych 12-fenylo-12H-chinoksalino-[2,3-b][1,4]-benzotiazyny o wzorze 1:The invention relates to compounds, 12-phenyl-12H-quinoxaline- [2,3-b] [1,4] -benzothiazine derivatives of the formula 1:
w którym R1 i R2 oznaczają niezależnie od siebie atom wodoru, chloru, bromu, grupę metylową, etylową, propylową, metoksylową lub etoksylową, R3 oznacza atom wodoru.wherein R1 and R2 are, independently of each other, hydrogen, chlorine, bromine, methyl, ethyl, propyl, methoxy or ethoxy, and R3 is hydrogen.
Związki według wynalazku stanowią sensybilizatory w parach fotoredoks ze związkami N-alkoksypirydyniowymi, trichlorometylo-1,3,5-triazynowymi lub difenylojodoniowymi i mają zastosowanie w procesie wolnorodnikowej, kationowej lub hybrydowej fotopolimeryzacji. Nadto, związki te mogą być stosowane jako barwniki fluoryzujące, gdyż wykazują duże wydajności kwantowe fluorescencji.The compounds of the invention are photoredox pairs sensitizers with N-alkoxy pyridinium, trichloromethyl-1,3,5-triazine or diphenyliodonium compounds and are used in free radical, cationic or hybrid photopolymerization processes. Moreover, these compounds can be used as fluorescent dyes because they show high quantum yields of fluorescence.
Związki, pochodne 12-fenylo-12H-chinoksalino-[2,3-b][1,4]-benzotiazyny, o wzorze 1 otrzymuje się sposobem według wynalazku, który polega na tym, że związek o wzorze 2:The compounds, 12-phenyl-12H-quinoxalino- [2,3-b] [1,4] -benzothiazine derivatives of formula 1 are obtained by the process according to the invention, which consists in that the compound of formula 2:
w którym R1 i R2 mają wyżej podane znaczenie poddaje się reakcji z jodobenzenem w obecności węglanu sodu lub potasu w temperaturze 120-188°C w czasie 1-25 godzin. Po tym czasie oddestylowujewherein R1 and R2 are as defined above are reacted with iodobenzene in the presence of sodium or potassium carbonate at 120-188 ° C for 1-25 hours. After this time, it distills
PL 217 059 B1 się pod zmniejszonym ciśnieniem jodobenzen, a pozostałość, po ochłodzeniu do temperatury pokojowej, rozpuszcza się w rozpuszczalniku organicznym, jak chloroform, metanol, etanol, aceton, acetonitryl, odsącza powstały osad i z przesączu odparowuje rozpuszczalnik. Pozostałość po odparowaniu rozpuszczalnika stanowi związek o wzorze 1. Na 1 mol związku o wzorze 2 stosuje się 10 moli jodobenzenu, 10 moli węglanu sodu lub potasu oraz 1,5 mola miedzi.After cooling to room temperature, the residue is dissolved in iodobenzene, and the residue is dissolved in an organic solvent such as chloroform, methanol, ethanol, acetone, acetonitrile, the precipitate formed is filtered off, and the solvent is evaporated from the filtrate. The residue after evaporation of the solvent is a compound of formula 1. 10 moles of iodobenzene, 10 moles of sodium or potassium carbonate and 1.5 moles of copper are used per mole of the compound of formula II.
Przedmiot wynalazku ilustrują poniższe przykłady. Części podane w przykładach oznaczają części wagowe.The following examples illustrate the subject matter of the invention. The parts given in the examples are parts by weight.
P r z y k ł a d IP r z k ł a d I
2,5 części 12H-chinoksalino-[2,3-b][1,4]-benzotiazyny, 14 części węglanu potasu, 1,6 części miedzi rozpuszczono w 37,5 częściach jodobenzenu. Całość ogrzewano 14 godzin w temperaturze 188°C. Po tym czasie oddestylowano pod zmniejszonym ciśnieniem jodobenzen, a pozostałość, po ochłodzeniu do temperatury pokojowej, rozpuszczono w 200 częściach etanolu, powstały osad odsączono i z przesączu odparowano etanol. Otrzymano 3,0 części związku o wzorze 3 w postaci żółtego proszku i temperaturze topnienia 202°C.2.5 parts of 12H-quinoxaline- [2,3-b] [1,4] -benzothiazine, 14 parts of potassium carbonate, 1.6 parts of copper are dissolved in 37.5 parts of iodobenzene. It was heated for 14 hours at 188 ° C. After this time, iodobenzene was distilled off under reduced pressure, and the residue, after cooling to room temperature, was dissolved in 200 parts of ethanol, the resulting precipitate was filtered off and the ethanol was evaporated from the filtrate. 3.0 parts of the compound of formula 3 are obtained as a yellow powder with a melting point of 202 ° C.
wzór 3 1 formula 3 1
Widmo 1H NMR oraz widmo masowe Cl otrzymanego związku w pełni potwierdziły jego budowę. 1 H NMR spectrum and mass spectrum of the compound obtained Cl fully confirmed the structure.
1H NMR: 6,10-6,14 (m, 1H), 6,84-6,89 (m, 2H), 7,02-7,07 (m, 1H), 7,29-7,40 (m, 5H), 7,50-7,54 (m, 1H), 7,58-7,61 (m, 3H). 1 H NMR: 6,10-6,14 (m, 1H), 6.84-6.89 (m, 2H), 7.02-7.07 (m, 1H), 7.29-7.40 (m, 5H), 7.50-7.54 (m, 1H), 7.58-7.61 (m, 3H).
Cl: pik molekularny M = 328.Cl: molecular peak M = 328.
Wydajność kwantowa fluorescencji związku o wzorze 3 w acetonitrylu wynosi 1,0. Działanie fotoinicjujące otrzymanego związku potwierdziło zastosowanie go w kompozycji do polimeryzacji akrylanu etylu i triakrylanu trimetylopropanu (TMPTA), tlenku cykloheksenu oraz metakrylanu glicydylu światłem o długości fali 419 nm.The quantum fluorescence yield of the compound of formula 3 in acetonitrile is 1.0. The photoinitiating effect of the obtained compound was confirmed by its use in the composition for the polymerization of ethyl acrylate and trimethylpropane triacrylate (TMPTA), cyclohexene oxide and glycidyl methacrylate with light with a wavelength of 419 nm.
P r z y k ł a d IIP r z x l a d II
2,79 części 3,4-dimetylo-12H-chinoksaIino-[2,3-b][1,4]-benzotiazyny, 10,6 części węglanu sodu, 1,6 części miedzi rozpuszczono w 37,5 częściach jodobenzenu. Całość ogrzewano 12 godzin w temperaturze 188°C. Po tym czasie oddestylowano pod zmniejszonym ciśnieniem jodobenzen i pozostałość, po ochłodzeniu do temperatury pokojowej, rozpuszczono w 250 częściach acetonu, odsączono powstały osad i z przesączu odparowano aceton. Otrzymano 3,1 części związku o wzorze 4:2.79 parts of 3,4-dimethyl-12H-quinoxaIino- [2,3-b] [1,4] benzothiazine, 10.6 parts of sodium carbonate, 1.6 parts of copper are dissolved in 37.5 parts of iodobenzene. It was heated for 12 hours at 188 ° C. After this time, iodobenzene was distilled off under reduced pressure and the residue, after cooling to room temperature, was dissolved in 250 parts of acetone, the precipitate formed was filtered off and acetone was evaporated from the filtrate. 3.1 parts of the compound of formula 4 were obtained:
w postaci żółtego proszku i temperaturze topnienia 235-236°C.as a yellow powder, mp 235-236 ° C.
11
Widmo 1H NMR oraz widmo masowe Cl otrzymanego związku w pełni potwierdziły jego budowę. 1H NMR: 2,25 (s, 3H), 2,32 (s, 3H) 6,07-6,14 (m, 1H), 6,75-6,89 (m, 2H), 7,02-7,07 (m, 1H), 1 H NMR spectrum and mass spectrum of the compound obtained Cl fully confirmed the structure. 1 H NMR: 2.25 (s, 3H), 2.32 (s, 3H), 6,07-6,14 (m, 1H), 6,75-6,89 (m, 2H), 7.02 -7.07 (m, 1H).
7,10 (s, 1H), 7,34-7,39 (m, 3H), 7,43-7,53 (m, 1H), 7,53-7,68 (m, 2H).7.10 (s, 1H), 7.34-7.39 (m, 3H), 7.43-7.53 (m, 1H), 7.53-7.68 (m, 2H).
PL 217 059 B1PL 217 059 B1
Zarejestrowany w widmie masowym Cl: pik molekularny = 355.Recorded in the Cl mass spectrum: molecular peak = 355.
Wydajność kwantowa fluorescencji związku o wzorze 4 w acetonitrylu wynosi 1,0. Działanie fotoinicjujące otrzymanego związku potwierdziło zastosowanie go w kompozycji do polimeryzacji akrylanu etylu i triakrylanu trimetylopropanu (TMPTA), tlenku cyklolieksenu oraz metakrylanu glicydylu światłem o długości fali 419 nm.The quantum yield of the fluorescence of the compound of formula 4 in acetonitrile is 1.0. The photoinitiating effect of the obtained compound was confirmed by its use in the composition for the polymerization of ethyl acrylate and trimethylpropane triacrylate (TMPTA), cyclolyxene oxide and glycidyl methacrylate with light with a wavelength of 419 nm.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL398084A PL217059B1 (en) | 2012-02-13 | 2012-02-13 | Compounds, derivatives of 12-phenyl-12H-quinoxaline-[2,3-b] [1,4] benzothiazine and the process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL398084A PL217059B1 (en) | 2012-02-13 | 2012-02-13 | Compounds, derivatives of 12-phenyl-12H-quinoxaline-[2,3-b] [1,4] benzothiazine and the process for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL398084A1 PL398084A1 (en) | 2013-08-19 |
| PL217059B1 true PL217059B1 (en) | 2014-06-30 |
Family
ID=48951735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL398084A PL217059B1 (en) | 2012-02-13 | 2012-02-13 | Compounds, derivatives of 12-phenyl-12H-quinoxaline-[2,3-b] [1,4] benzothiazine and the process for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL217059B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108250213A (en) * | 2017-12-26 | 2018-07-06 | 中节能万润股份有限公司 | A kind of preparation and its application of novel OLED electron transport materials |
-
2012
- 2012-02-13 PL PL398084A patent/PL217059B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108250213A (en) * | 2017-12-26 | 2018-07-06 | 中节能万润股份有限公司 | A kind of preparation and its application of novel OLED electron transport materials |
Also Published As
| Publication number | Publication date |
|---|---|
| PL398084A1 (en) | 2013-08-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2981520B1 (en) | New process for the synthesis of 1-(2-((2,4-dimethylphenyl)thio)phenyl)piperazine | |
| EP2670751B1 (en) | Methods of making hiv attachment inhibitor prodrug compound and intermediates | |
| JP2015536944A (en) | Strong fluorescent luminescent heterocyclic compound and method for producing the same | |
| CN102040617B (en) | Organic boron difluoride complex and preparation method thereof | |
| CA2760384A1 (en) | Process for the preparation of [4-(2-chloro-4-methoxy-5-methylphenyl)-5-methyl-thiazolo-2-yl]-[2-cyclopropyl-1-(3-fluoro-4-methylphenyl)-ethyl]-amine | |
| WO2012174685A1 (en) | Preparation method of 2-substituted-2h-1,2,3-triazole derivative | |
| PL217059B1 (en) | Compounds, derivatives of 12-phenyl-12H-quinoxaline-[2,3-b] [1,4] benzothiazine and the process for their preparation | |
| KR101855334B1 (en) | Preparation method of intermediate of oxazolidinone derivatives | |
| Padalkar et al. | Excited-state intramolecular proton transfer (ESIPT) inspired azole-quinoline based fluorophores: Synthesis and photophysical properties study | |
| JP6251197B2 (en) | Process for preparing substituted phenylpropanones | |
| CN112390725B (en) | Preparation method of amide compound | |
| Wang et al. | Facile synthesis and fluorescent properties of coumarin-7 and its isomer 4-(2-benzimidazolyl)-7-(diethylamino) coumarin | |
| JP5288779B2 (en) | 2,3-dicyanonaphthalene derivative | |
| CN101168530A (en) | 1,4-dioxoquinoxaline formaldehyde dihydrazone with herbicidal activity and its preparation method and application | |
| CN100579971C (en) | The preparation method of terbuthiauron | |
| CN110023296A (en) | 4-((6-(2-(2,4-Difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-mercapto-1H-1,2,4-triazole-1 -yl)propyl)pyridin-3-yl)oxy)benzonitrile and preparation method | |
| JP2006188582A (en) | Novel pyrazolone compound and merocyanine dye using the same | |
| CN102993194B (en) | Cyanuric-chloride-based benzothiazole ESIPT compounds, and preparation method and purpose thereof | |
| KR20190043743A (en) | Dicyanstyryl benzene derivatives and fluorescent material comprising the same | |
| JP2005314377A (en) | Method for producing bipyridinium compound | |
| JP2017088879A (en) | Method for producing aminobenzopyranoxanthene (ABPX) dye compound | |
| WO2014031581A1 (en) | Process for the synthesis of substituted gamma lactams | |
| KR101009404B1 (en) | (S) -ene- (1-carboxy-2-methyl-pro-1-fil) -ene-pentanoyl-ene- [2 '-(1H-tetrazol-5-yl) biphenyl-4-yl -Purity preparation method of -methyl] amine compound | |
| CN101265256A (en) | Tetrastyryl biscarbazole compound and preparation method thereof | |
| DE102013012685A1 (en) | Arylated pyrazole derivatives and their use as fluorescent dyes |