GB828847A - Improvements in or relating to cyanine dyes - Google Patents
Improvements in or relating to cyanine dyesInfo
- Publication number
- GB828847A GB828847A GB3824456A GB3824456A GB828847A GB 828847 A GB828847 A GB 828847A GB 3824456 A GB3824456 A GB 3824456A GB 3824456 A GB3824456 A GB 3824456A GB 828847 A GB828847 A GB 828847A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- acid
- group
- phenyl
- prepared
- 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 7
- 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
- 150000001875 compounds Chemical class 0.000 abstract 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 5
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- -1 tetronic acid aryl hydrazones Chemical class 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000004391 aryl sulfonyl 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000001589 carboacyl group Chemical group 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
- 125000003710 aryl alkyl group 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
- PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 abstract 2
- 229940067157 phenylhydrazine Drugs 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- RWNMLYACWNIEIG-UHFFFAOYSA-N 5,6-dimethyl-1,3-benzoxazole Chemical compound C1=C(C)C(C)=CC2=C1OC=N2 RWNMLYACWNIEIG-UHFFFAOYSA-N 0.000 abstract 1
- QIMPUUHZJZDPCA-UHFFFAOYSA-N 5-(hydroxymethyl)-2-phenyl-4h-pyrazol-3-one Chemical compound O=C1CC(CO)=NN1C1=CC=CC=C1 QIMPUUHZJZDPCA-UHFFFAOYSA-N 0.000 abstract 1
- SEBIXVUYSFOUEL-UHFFFAOYSA-N 5-methyl-1,3-benzothiazole Chemical compound CC1=CC=C2SC=NC2=C1 SEBIXVUYSFOUEL-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
- FKYKJYSYSGEDCG-UHFFFAOYSA-N 6-methoxy-1,3-benzoxazole Chemical compound COC1=CC=C2N=COC2=C1 FKYKJYSYSGEDCG-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 1
- 150000001450 anions Chemical group 0.000 abstract 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 150000002905 orthoesters Chemical class 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Compounds of the general formula <FORM:0828847/IV (b)/1> wherein R1 is hydrogen or an aryl group, R2 is hydrogen or a carboxylic acyl or arylsulphonyl group, and R3 is an aryl or substituted aryl group, are prepared by the base-catalysed rearrangement of tetronic acid aryl hydrazones of the formula <FORM:0828847/IV (b)/2> to give compounds wherein R2 is H, followed by acylation, if required, to give compounds wherein R2 is carboxylic acyl or arylsulphonyl. An example is given of the preparation of 3-a -hydroxybenzyl-1-phenyl-5-pyrazolone from g -phenyltetronic acid phenylhydrazone using sodium ethoxide. 3-a -Hydroxymethyl- and 3-a -hydroxybenzyl - 1 - p - chlorophenyl - 5 - pyrazolones are similarly prepared. An example also is given of the treatment of tetronic acid phenyl hydrazone with sodium ethoxide to give 3-hydroxymethyl-1-phenyl-5-pyrazolone which is not isolated. Tetronic acid phenylhydrazone is prepared by dissolving a -ethoxycarbonyl-tetronic acid in aqueous caustic soda, acidifying with conc. HCl whereupon CO2 is evolved, and treating the product at 0 DEG C. with phenylhydrazine in the presence of sodium acetate and acetic acid. Tetronic acid - p - chlorophenylhydrazone is similarly prepared. g -Phenyltetronic acid phenylhydrazone is prepared by dissolving g -phenyltetronic acid in aqueous acetic acid and adding phenylhydrazine. g - Phenyltetronic acid - p - chlorophenylhydrazine is similarly prepared. According to the Provisional Specification, R1 may be alkyl or aralkyl.ALSO:Merocyanine dyes of the general formula <FORM:0828847/IV(c)/1> wherein R1 is hydrogen or an aryl group, R2 is hydrogen or a carboxylic acyl or arylsulphonyl group, R3 is an aryl or substituted aryl group, R4 is hydrogen or an alkyl group, R5 is an alkyl, hydroxyalkyl or aryl group, m and n are 0 or 1 and D completes a 5- or 6-membered heterocyclic nucleus, are prepared (i) for dyes wherein R4 is methyl or ethyl; by reacting an ortho ester of the formula R4C(OC2H5)3 with a compound of the formula <FORM:0828847/IV(c)/2> and a compound of the formula <FORM:0828847/IV(c)/3> wherein X is an anion; (ii) for dyes wherein R2 is H ; by reacting a base such as sodium ethoxide with a tetronic acid aryl hydrazone of the formula <FORM:0828847/IV(c)/4> whereby a pyrazolone of formula 1 above is formed in situ (or by starting with a compound of formula I), and then reacting this with a compound of formula <FORM:0828847/IV(c)/5> wherein Y is an alkylthio, alkylthiovinyl, alkylthiopropenyl or higher homologous group, or an acetanilidovinyl group; (iii) for dyes wherein R2 is acyl or arylsulphonyl ; by treating a dye wherein R2 is H with an acylating agent such as acetic anhydride or benzoyl chloride or an arylsulphonyl chloride such as toluene-p-sulphonyl chloride. Examples are given of the preparation of dyes wherein R1 is H or phenyl, R2 is H, acetyl, benzoyl or toluene-p-sulphonyl, R3 is phenyl or p-chlorophenyl, R4 is H or methyl, R5 is methyl or ethyl, and D completes an indole, benzthiazole, 5-methyl-benzthiazole, benzoxazole, 6 - methoxy - benzoxazole, 5,6-dimethyl - benzoxazole, 5 - phenyl - benzoxazole, 2 - quinoline or 4 - quinoline nucleus. According to the Provisional Specification, R1 may be alkyl or aralkyl.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3824456A GB828847A (en) | 1956-12-14 | 1956-12-14 | Improvements in or relating to cyanine dyes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3824456A GB828847A (en) | 1956-12-14 | 1956-12-14 | Improvements in or relating to cyanine dyes |
Publications (1)
Publication Number | Publication Date |
---|---|
GB828847A true GB828847A (en) | 1960-02-24 |
Family
ID=10402204
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3824456A Expired GB828847A (en) | 1956-12-14 | 1956-12-14 | Improvements in or relating to cyanine dyes |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB828847A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006023931A2 (en) * | 2004-08-18 | 2006-03-02 | Takeda San Diego, Inc. | Kinase inhibitors |
US7713973B2 (en) | 2004-10-15 | 2010-05-11 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
US8278450B2 (en) | 2007-04-18 | 2012-10-02 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
-
1956
- 1956-12-14 GB GB3824456A patent/GB828847A/en not_active Expired
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006023931A2 (en) * | 2004-08-18 | 2006-03-02 | Takeda San Diego, Inc. | Kinase inhibitors |
WO2006023931A3 (en) * | 2004-08-18 | 2006-05-18 | Takeda San Diego Inc | Kinase inhibitors |
JP2008510734A (en) * | 2004-08-18 | 2008-04-10 | タケダ サン ディエゴ インコーポレイテッド | Kinase inhibitor |
US7713973B2 (en) | 2004-10-15 | 2010-05-11 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
US8288536B2 (en) | 2004-10-15 | 2012-10-16 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
US8278450B2 (en) | 2007-04-18 | 2012-10-02 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
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