GB874204A - Improvements in or relating to triazaindolizine compounds - Google Patents
Improvements in or relating to triazaindolizine compoundsInfo
- Publication number
- GB874204A GB874204A GB296357A GB296357A GB874204A GB 874204 A GB874204 A GB 874204A GB 296357 A GB296357 A GB 296357A GB 296357 A GB296357 A GB 296357A GB 874204 A GB874204 A GB 874204A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- hydrogen
- formula
- aralkyl
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title abstract 14
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 4
- 125000004659 aryl alkyl thio group Chemical group 0.000 abstract 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000004414 alkyl thio group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- 235000019253 formic acid Nutrition 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- -1 mercapto compound Chemical class 0.000 abstract 2
- OHTQJGFJIGBWGE-UHFFFAOYSA-N 2-[2-[bis(methylsulfanyl)methylidene]hydrazinyl]-4-methyl-1H-pyrimidin-6-one Chemical compound CC1=NC(=NC(=C1)O)NN=C(SC)SC OHTQJGFJIGBWGE-UHFFFAOYSA-N 0.000 abstract 1
- RFKCQKWRFAJRPY-UHFFFAOYSA-N 2-hydrazinyl-6-methyl-1h-pyrimidin-4-one Chemical compound CC1=CC(=O)N=C(NN)N1 RFKCQKWRFAJRPY-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 239000012435 aralkylating agent Substances 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 229940087646 methanolamine Drugs 0.000 abstract 1
- 150000007530 organic bases Chemical group 0.000 abstract 1
- 229910052709 silver Inorganic materials 0.000 abstract 1
- 239000004332 silver Substances 0.000 abstract 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
The invention comprises triazaindolizine compounds of formulae <FORM:0874204/IV (b)/1> or <FORM:0874204/IV (b)/2> or tautomers thereof, where R1 is hydrogen or a mercapto, alkythio or aralkylthio group (but not hydrogen in the second formula), R2 is hydrogen, alkyl, aralkyl, aryl or heterocyclic, R3 is hydrogen, alkyl or aralkyl, or R2 and R3 together make up the residue of an alicyclic or benzene ring. Compounds wherein R1 is mercapto may be prepared by reacting CS2 with a compound of formula <FORM:0874204/IV (b)/3> in the presence of a secondary or tertiary organic base and an alcohol as diluent. Compounds in which R1 is alkylthio or aralkylthio may be obtained by treating the corresponding alkali metal mercaptide with a molecular equivalent of an alkylating or aralkylating agent. Compounds of the first formula in which R1 is hydrogen may be prepared by the catalytic reduction of the corresponding mercapto compound with a Raney nickel catalyst containing adsorbed hydrogen. Compounds of the first formula given above wherein R1 is hydrogen and R2 and R3 together make up the residue of a benzene ring may be prepared by the reaction of formic acid (or, according to the first Provisional Specification, an anhydride of an aliphatic or aromatic carboxylic acid) with a compound of formula <FORM:0874204/IV (b)/4> Compounds of the first formula given above wherein R1 is alkylthio or aralkylthio may be obtained by heating to a temperature above its melting point a compound of formula <FORM:0874204/IV (b)/5> where R4 is alkyl or aralkyl; these compounds, when boiled in glacial acetic acid, yield compounds of the first formula given above (R1 being alkylthio or aralkylthio). According to the first Provisional Specification, when R2 and R3 together make up a benzene residue, R1 may also be alkyl, aralkyl or aryl; these values for R1 do not appear in the Complete Specification; these compounds may be prepared by reacting 2-hydrazino-4-hydroxyquinoazoline with formic acid or an anhydride of an aliphatic or aromatic carboxylic acid; and an additional example is given. The triethylamine salt of 2-(4-methyl-6-hydroxy-2-pyrimidyl)-dithiocarbazinic acid is obtained as a by-product when reacting 4-methyl-6-hydroxy-2-pyrimidylhydrazine with CS2, methanol and triethylamine. It is methylated with methyl iodide to yield 4-methyl-6-hydroxy-2[bis(methylthio)methylene hydrazino] -pyrimidine. The compounds of the invention are used in photographic silver halide emulsions (see Group XX). Specifications 851,815 and 851,816 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB296357A GB874204A (en) | 1957-01-28 | 1957-01-28 | Improvements in or relating to triazaindolizine compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB296357A GB874204A (en) | 1957-01-28 | 1957-01-28 | Improvements in or relating to triazaindolizine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB874204A true GB874204A (en) | 1961-08-02 |
Family
ID=9749327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB296357A Expired GB874204A (en) | 1957-01-28 | 1957-01-28 | Improvements in or relating to triazaindolizine compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB874204A (en) |
-
1957
- 1957-01-28 GB GB296357A patent/GB874204A/en not_active Expired
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