GB862825A - Improvements in or relating to cyanine and merocyanine dyes - Google Patents
Improvements in or relating to cyanine and merocyanine dyesInfo
- Publication number
- GB862825A GB862825A GB417357A GB417357A GB862825A GB 862825 A GB862825 A GB 862825A GB 417357 A GB417357 A GB 417357A GB 417357 A GB417357 A GB 417357A GB 862825 A GB862825 A GB 862825A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- methyl
- alkyl
- ethyl
- compound
- 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.)
- Expired
Links
- 239000000975 dye Substances 0.000 title abstract 4
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 title 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 8
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 150000003839 salts Chemical group 0.000 abstract 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 150000001450 anions Chemical group 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 abstract 1
- UPCYEFFISUGBRW-UHFFFAOYSA-N 3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one Chemical group CCN1C(=O)CSC1=S UPCYEFFISUGBRW-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- YTSFYTDPSSFCLU-UHFFFAOYSA-N 5-chloro-1,3-benzothiazole Chemical compound ClC1=CC=C2SC=NC2=C1 YTSFYTDPSSFCLU-UHFFFAOYSA-N 0.000 abstract 1
- FWNHUZOBVQZERU-UHFFFAOYSA-N 5-methyl-1h-pyrazole-3-carbohydrazide Chemical compound CC1=CC(C(=O)NN)=NN1 FWNHUZOBVQZERU-UHFFFAOYSA-N 0.000 abstract 1
- NIFNXGHHDAXUGO-UHFFFAOYSA-N 5-phenyl-1,3-benzoxazole Chemical compound C=1C=C2OC=NC2=CC=1C1=CC=CC=C1 NIFNXGHHDAXUGO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- GFIGSHYZTSXVRD-UHFFFAOYSA-N 6-ethoxy-1,3-benzoxazole Chemical compound CCOC1=CC=C2N=COC2=C1 GFIGSHYZTSXVRD-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910019213 POCl3 Inorganic materials 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- -1 cyclic ketomethylene compound Chemical class 0.000 abstract 1
- UVJQQYMWMAISMQ-UHFFFAOYSA-N ethyl 2,4-dioxo-4-phenylbutanoate Chemical compound CCOC(=O)C(=O)CC(=O)C1=CC=CC=C1 UVJQQYMWMAISMQ-UHFFFAOYSA-N 0.000 abstract 1
- OYQVQWIASIXXRT-UHFFFAOYSA-N ethyl 2,4-dioxopentanoate Chemical compound CCOC(=O)C(=O)CC(C)=O OYQVQWIASIXXRT-UHFFFAOYSA-N 0.000 abstract 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000002927 oxygen compounds Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 abstract 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Compounds of the general formula:- <FORM:0862825/IV (b)/1> wherein Rc is an alkyl or aryl group and A is O, are prepared in the enolic form by treating a compound of the formula:- <FORM:0862825/IV (b)/2> with acetic anhydride and a strong acid catalyst such as phosphoric or sulphuric acid. Examples are given of the preparation of 2-methyl- and 2-phenyl-4-hydroxy-7-methyl-1; 5; 6-triazaindolizines. Compounds of the general formula VIII wherein A is S are prepared by treating the corresponding oxygen compounds with phosphorus pentasulphide. 2; 7-Dimethyl-4-mercapto- 1:5:6-triazaindolizine and 2-phenyl-4-mercapto-7-methyl-1:5:6-triazaindolizine are produced in this way. By treating the 4-mercapto compounds with an alkyl or aralkyl salt, 4-alkylthio- or 4-aralkylthio-triazaindolizines are produced. Examples are given of the preparation of the 4-methylthio, 4-ethylthio- and 4-benzylthio- 2:7-dimethyl 1; 5; 6-triazaindolizines and 2-phenyl-4-methylthio-7-methyl- 1; 5; 6- triazaindolizine. The corresponding 4-alkoxy or 4-aralkoxy compounds are prepared by treating the compounds of formula VIII (A=O), e.g. with POCl3, to give the 4-chloro compound, with is then reacted with the sodium salt of an alcohol, NaORa (Ra=alkyl or aralkyl). By this method 4-methoxy-2:7-dimethyl-1:5:6-triazaindolizine is prepared from the corresponding 4-chloro-compound. Quaternary salts of the general formula:- <FORM:0862825/IV (b)/3> wherein R and Ra are alkyl or aralkyl, Rc is alkyl or aryl, A is O or S and X is an anion, are prepared by treating the bases, prepared as described above, with a compound RX, such as methyl iodide or ethyl iodide. 3-Methylpyrazole-5-carbohydrazide is prepared from ethyl acetopyruvate and hydrazine hydrate. The corresponding 3-phenylcompound is similarly prepared from ethyl benzoylpyruvate.ALSO:Methine dyes having one of the general formulae:- <FORM:0862825/IV(c)/1> wherein R, Ra and Rb are alkyl or aralkyl groups, Rc is alkyl or aryl, A is O or S, n is 0 or 1, X is an anion and Da and Db complete 5- or 6-membered heterocyclic nuclei, are prepared by reacting a 2; 4-substituted-7-methyl-1; 5; 6-triazaindolizinium quaternary salt with a cyclammonium quaternary salt having a reactive a -thioether, thioethervinyl or acetanilidovinyl group, or with a compound of the formula:- <FORM:0862825/IV(c)/2> The latter compound may be replaced by a cyclic ketomethylene compound and ethyl orthoformate. Symmetrical trimethine dyes may be prepared from 2 mols of the triazaindolizinium acid and one mol of an alkyl orthoformate. Examples are given of the preparation of dyes wherein R and Rb are methyl or ethyl, Ra is methyl, ethyl or benzyl, Rc is methyl or phenyl, Da completes a benzthiazole, 5-chlorobenzthiazole, a -naphthathiazole, benzoxazole, 5-phenyl-benzoxazole, 6-ethoxybenzoxazole, 5; 6-dimethyl-benzoxazole, thiazoline, pyrroline, 3; 3-dimethyl-indolenine or 1; 5; 6-triazaindolizine nucleus, and Db is 3-ethyl-rhodanine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB417357A GB862825A (en) | 1957-02-06 | 1957-02-06 | Improvements in or relating to cyanine and merocyanine dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB417357A GB862825A (en) | 1957-02-06 | 1957-02-06 | Improvements in or relating to cyanine and merocyanine dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB862825A true GB862825A (en) | 1961-03-15 |
Family
ID=9772077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB417357A Expired GB862825A (en) | 1957-02-06 | 1957-02-06 | Improvements in or relating to cyanine and merocyanine dyes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB862825A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021209552A1 (en) * | 2020-04-15 | 2021-10-21 | Janssen Pharmaceutica Nv | Pyrazolo[1,5-d][1,2,4]triazine-5(4h)-acetamides as inhibitors of the nlrp3 inflammasome pathway |
-
1957
- 1957-02-06 GB GB417357A patent/GB862825A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021209552A1 (en) * | 2020-04-15 | 2021-10-21 | Janssen Pharmaceutica Nv | Pyrazolo[1,5-d][1,2,4]triazine-5(4h)-acetamides as inhibitors of the nlrp3 inflammasome pathway |
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