GB828847A - Improvements in or relating to cyanine dyes - Google Patents

Improvements in or relating to cyanine dyes

Info

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
Application number
GB3824456A
Inventor
George Frank Duffin
John David Kendall
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.)
Ilford Imaging UK Ltd
Original Assignee
Ilford Ltd
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 Ilford Ltd filed Critical Ilford Ltd
Priority to GB3824456A priority Critical patent/GB828847A/en
Publication of GB828847A publication Critical patent/GB828847A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10The 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.
GB3824456A 1956-12-14 1956-12-14 Improvements in or relating to cyanine dyes Expired GB828847A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (7)

* Cited by examiner, † Cited by third party
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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