GB713540A - Improvements in and relating to 1:2:4-triazine derivatives - Google Patents
Improvements in and relating to 1:2:4-triazine derivativesInfo
- Publication number
- GB713540A GB713540A GB18060/51A GB1806051A GB713540A GB 713540 A GB713540 A GB 713540A GB 18060/51 A GB18060/51 A GB 18060/51A GB 1806051 A GB1806051 A GB 1806051A GB 713540 A GB713540 A GB 713540A
- Authority
- GB
- United Kingdom
- Prior art keywords
- glyoxylic acid
- thiosemicarbazide
- triazine
- aminophenyl
- nitrophenyl
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 11
- -1 nitro, amino, substituted amino Chemical group 0.000 abstract 9
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 abstract 4
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 abstract 2
- FSFFJEWAYWRLFT-UHFFFAOYSA-N ethyl 2-(4-methoxyphenyl)-2-oxoacetate Chemical compound CCOC(=O)C(=O)C1=CC=C(OC)C=C1 FSFFJEWAYWRLFT-UHFFFAOYSA-N 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 150000003584 thiosemicarbazones Chemical class 0.000 abstract 2
- ZNTIQRYMOADNDC-UHFFFAOYSA-N 2-(4-aminophenyl)-2-oxoacetic acid Chemical compound NC1=CC=C(C(=O)C(O)=O)C=C1 ZNTIQRYMOADNDC-UHFFFAOYSA-N 0.000 abstract 1
- HUEVGNSRSURRKC-UHFFFAOYSA-N 2-(carbamothioylhydrazinylidene)-2-(4-nitrophenyl)acetic acid Chemical compound NC(=S)NN=C(C(O)=O)C1=CC=C([N+]([O-])=O)C=C1 HUEVGNSRSURRKC-UHFFFAOYSA-N 0.000 abstract 1
- RREPYIWLDJQENS-UHFFFAOYSA-N 4-nitrophenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=C([N+]([O-])=O)C=C1 RREPYIWLDJQENS-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- BPMAWNXZKVCVOU-UHFFFAOYSA-N NC1=CC=C(C=C1)C(C(=O)O)=NNC(=S)N Chemical compound NC1=CC=C(C=C1)C(C(=O)O)=NNC(=S)N BPMAWNXZKVCVOU-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical class OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds having one of the general formul <FORM:0713540/IV (b)/1> wherein R represents a phenyl radical substituted by at least one alkyl, alkoxy, alkylmercapto, alkylsulphonyl, halogen, nitro, amino, substituted amino, acylamino (including sulphonamido), ureido, thioureido, hydroxy, acyloxy or alkoxycarbonylamino radical. They can be prepared by treating thiosemicarbazones of a -ketonic acids of the general formula <FORM:0713540/IV (b)/2> or their reactive functional derivatives with ring-forming agents, as which being specified alkalies, e.g. sodium or potassium carbonate or sodium hydroxide. The thiosemicarbazones are obtained by reacting thiosemicarbazide with the appropriately substituted phenylglyoxylic acid. In examples (1) 6-(41-methoxyphenyl)-3-mercapto - 1 : 2 : 4 - triazine - 5 - (2H) - one is produced by refluxing with potassium carbonate solution 4-methoxyphenyl glyoxylic acid ethyl ester (from 4-methoxyphenyl glyoxylic acid ethyl ester and thiosemicarbazide; (2) 6-(41-aminophenyl) - 3 - mercapto - 1 : 2 : 4 - triazine-5-(2H)- one is produced by heating 4-aminophenyl glyoxylic acid thiosemicarbazone (from 4-aminophenyl glyoxylic acid and thiosemicarbazide) with dilute caustic soda lye. The product is acetylated to the corresponding 41-acetamino derivative; (3) 6-(41-nitrophenyl)-3-mercapto - 1 : 2 : 4 - triazine - 5 - (2H) - one is obtained by allowing 4-nitrophenyl glyoxylic acid thiosemicarbazone (from 4-nitrophenyl glyoxylic acid and thiosemicarbazide) to stand with caustic soda solution. The product is reduced to the corresponding p 41-amino-compound. A table is given of compounds of the second formula above where R represents a phenyl radical substituted in the p-position by chlorine or bromine or a hydroxy, b -hydroxyethoxy-, methylmercapto, methylsulphonyl, ethylsulphonyl, ethyl, b : b -dimethylacryloylamino, benzoylamino, p-methylbenzoylamino, ethoxycarbonylamino, N1 - methyl - thioureido, N1-ethylureido, methylsulphonamido or a benzylideneimino group or in which R represents a 2 : 4 - dihydroxyphenyl, 3 - methoxy - 4-hydroxphenyl, or 3-methoxy-4-methylphenyl radical.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH713540X | 1950-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB713540A true GB713540A (en) | 1954-08-11 |
Family
ID=4530955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18060/51A Expired GB713540A (en) | 1950-08-01 | 1951-07-31 | Improvements in and relating to 1:2:4-triazine derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB713540A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220767A (en) * | 1977-03-19 | 1980-09-02 | Smith Kline & French Laboratories Limited | Triazinones |
-
1951
- 1951-07-31 GB GB18060/51A patent/GB713540A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220767A (en) * | 1977-03-19 | 1980-09-02 | Smith Kline & French Laboratories Limited | Triazinones |
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