DE10206366A1 - Cyclische Verbindungen und ihre Verwendung als Komplexliganden - Google Patents
Cyclische Verbindungen und ihre Verwendung als KomplexligandenInfo
- Publication number
- DE10206366A1 DE10206366A1 DE10206366A DE10206366A DE10206366A1 DE 10206366 A1 DE10206366 A1 DE 10206366A1 DE 10206366 A DE10206366 A DE 10206366A DE 10206366 A DE10206366 A DE 10206366A DE 10206366 A1 DE10206366 A1 DE 10206366A1
- Authority
- DE
- Germany
- Prior art keywords
- compound
- cyclic
- compounds
- general formula
- alkyl
- 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.)
- Withdrawn
Links
- 150000001923 cyclic compounds Chemical class 0.000 title claims abstract description 18
- 239000003446 ligand Substances 0.000 title claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 39
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910021645 metal ion Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- KHGLJFGSFNGDCE-UHFFFAOYSA-N 3-amino-2-hydroxybenzamide Chemical compound NC(=O)C1=CC=CC(N)=C1O KHGLJFGSFNGDCE-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- KKTUQAYCCLMNOA-UHFFFAOYSA-N 2,3-diaminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1N KKTUQAYCCLMNOA-UHFFFAOYSA-N 0.000 description 4
- JJPIVRWTAGQTPQ-UHFFFAOYSA-N 2-amino-3-nitrobenzoic acid Chemical compound NC1=C(C(O)=O)C=CC=C1[N+]([O-])=O JJPIVRWTAGQTPQ-UHFFFAOYSA-N 0.000 description 4
- FECMDSYYFNKSJZ-UHFFFAOYSA-N 2-hydroxy-3-nitrobenzamide Chemical compound NC(=O)C1=CC=CC([N+]([O-])=O)=C1O FECMDSYYFNKSJZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 150000003983 crown ethers Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- NIBVYEHAFBEVFI-UHFFFAOYSA-N methyl 2-hydroxy-3-nitrobenzoate Chemical compound COC(=O)C1=CC=CC([N+]([O-])=O)=C1O NIBVYEHAFBEVFI-UHFFFAOYSA-N 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- PARGTJDYVRRGDB-UHFFFAOYSA-N 2-amino-6-(3-amino-2-hydroxyphenyl)phenol Chemical compound NC1=CC=CC(C=2C(=C(N)C=CC=2)O)=C1O PARGTJDYVRRGDB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000013081 microcrystal Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 150000004032 porphyrins Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QYGVENSBTDTZTN-UHFFFAOYSA-N 7-(1,3-benzoxazol-7-yl)-1,3-benzoxazole Chemical group C=12OC=NC2=CC=CC=1C1=CC=CC2=C1OC=N2 QYGVENSBTDTZTN-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- -1 amino compound Chemical class 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Chemical group 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10206366A DE10206366A1 (de) | 2002-02-15 | 2002-02-15 | Cyclische Verbindungen und ihre Verwendung als Komplexliganden |
| JP2003567906A JP2005525343A (ja) | 2002-02-15 | 2003-02-14 | 環式化合物及び錯配位子としてのその使用 |
| AU2003205767A AU2003205767A1 (en) | 2002-02-15 | 2003-02-14 | Cyclic compounds and their use as complex ligands |
| PCT/EP2003/001490 WO2003068779A1 (de) | 2002-02-15 | 2003-02-14 | Cyclische verbindungen und ihre verwendung als komplexliganden |
| EP03702641A EP1476447A1 (de) | 2002-02-15 | 2003-02-14 | Cyclische verbindungen und ihre verwendung als komplexliganden |
| US10/503,587 US20050159596A1 (en) | 2002-02-15 | 2003-02-14 | Cyclic compounds and their use as complex ligands |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10206366A DE10206366A1 (de) | 2002-02-15 | 2002-02-15 | Cyclische Verbindungen und ihre Verwendung als Komplexliganden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10206366A1 true DE10206366A1 (de) | 2003-08-28 |
Family
ID=27634999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10206366A Withdrawn DE10206366A1 (de) | 2002-02-15 | 2002-02-15 | Cyclische Verbindungen und ihre Verwendung als Komplexliganden |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20050159596A1 (enExample) |
| EP (1) | EP1476447A1 (enExample) |
| JP (1) | JP2005525343A (enExample) |
| AU (1) | AU2003205767A1 (enExample) |
| DE (1) | DE10206366A1 (enExample) |
| WO (1) | WO2003068779A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10214937A1 (de) * | 2002-04-04 | 2003-10-16 | Basf Ag | Cyclische Verbindungen und ihre Verwendung als Lichtabsorber, Lichtemitter oder Komplexliganden |
| FI20040592L (fi) | 2004-04-27 | 2005-10-28 | Imbera Electronics Oy | Lämmön johtaminen upotetusta komponentista |
| CN116925092B (zh) * | 2022-04-11 | 2025-11-25 | 中国科学院理化技术研究所 | 酞菁络合物、其制备、包含该酞菁络合物的酞菁-载体材料及其制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH476793A (de) * | 1964-09-01 | 1969-08-15 | Ciba Geigy | Verwendung von neuen Bis-azolen als optische Aufhellmittel ausserhalb der Textilindustrie |
| US3481945A (en) * | 1966-12-09 | 1969-12-02 | Moleculon Corp | Tetrabenzimidazole |
| US5180821A (en) * | 1990-01-16 | 1993-01-19 | Moleculon Research Company | Cyclic tetrabenzimidazole |
-
2002
- 2002-02-15 DE DE10206366A patent/DE10206366A1/de not_active Withdrawn
-
2003
- 2003-02-14 US US10/503,587 patent/US20050159596A1/en not_active Abandoned
- 2003-02-14 AU AU2003205767A patent/AU2003205767A1/en not_active Abandoned
- 2003-02-14 JP JP2003567906A patent/JP2005525343A/ja not_active Withdrawn
- 2003-02-14 WO PCT/EP2003/001490 patent/WO2003068779A1/de not_active Ceased
- 2003-02-14 EP EP03702641A patent/EP1476447A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003068779A1 (de) | 2003-08-21 |
| AU2003205767A1 (en) | 2003-09-04 |
| JP2005525343A (ja) | 2005-08-25 |
| EP1476447A1 (de) | 2004-11-17 |
| US20050159596A1 (en) | 2005-07-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |