GB705609A - Improvements in and relating to 1:2:4-triazine derivatives - Google Patents
Improvements in and relating to 1:2:4-triazine derivativesInfo
- Publication number
- GB705609A GB705609A GB18061/51A GB1806151A GB705609A GB 705609 A GB705609 A GB 705609A GB 18061/51 A GB18061/51 A GB 18061/51A GB 1806151 A GB1806151 A GB 1806151A GB 705609 A GB705609 A GB 705609A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- thienyl
- substituted
- furyl
- pyridyl
- 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
- 239000002253 acid Substances 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical group OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 abstract 3
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical group CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 abstract 2
- 125000002541 furyl group Chemical group 0.000 abstract 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 abstract 2
- 125000001041 indolyl group Chemical group 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 125000005493 quinolyl group Chemical group 0.000 abstract 2
- 125000001544 thienyl group Chemical group 0.000 abstract 2
- 150000003584 thiosemicarbazones Chemical class 0.000 abstract 2
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 abstract 1
- -1 8-hydroxyquinolyl Chemical group 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
- 239000003513 alkali Substances 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 229940107700 pyruvic acid Drugs 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
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises 1:2:4-triazine derivatives having one of the general formulae- <FORM:0705609/IV (b)/1> or <FORM:0705609/IV (b)/2> wherein R represents a substituted or unsubstituted heterocyclic radical. They can be obtained by treating thiosemicarbazones of a -ketonic acids having one of the general formulae- <FORM:0705609/IV (b)/3> or <FORM:0705609/IV (b)/4> or reactive functional derivatives thereof, with ring forming agents, as which are specified alkalies, e.g. sodium and potassium carbonate and sodium hydroxide. The thiosemicarbazones are obtained by reacting thiosemicarbazide and the a -ketonic acid or, in some case the a -thioketonic acid appropriately substituted by the radical R. As suitable a -ketonic acids are specified glyoxylic acid substituted at the a -carbon atom by furyl-(2) and-(3), 5-methylfuryl-(2)-, 5-nitro-furyl-(2), thienyl-(2) or (3)-, 5-chlorothienyl-(2), pyrryl-(2) and (3)-, N-methyl-pyrryl-(2)-, imidazolyl-(4)-, thiazolyl-(4)-, 2-aminothiazolyl-(4)-, benzofuryl-(2) and -(3)-, thionaphthenyl-(2)-and-(3)-, indolyl-(3)-, pyridyl-(2)- -(3) and -(4)-, and quinolyl -(2)-radicals; pyruvic acid substituted by furyl -(2) and -(3)-, thienyl-(2)-, 1:2:4-oxadiazolyl-(5)-, indolyl -(3)-, pyridyl -(2)-, (3) and (4)-, and quinolyl -(2)- and -(4)- radicals; indolyl -(3)-thiopyruvic acid; and furyl -(2)- thiopyruvic acid. In an example, 6-thienyl -3- mercapto -1:2:4-triazine -5- (2H)- one is obtained by boiling in alkaline solution thienyl -(2)- glyoxylic acid semicarbazone (obtained from, e.g. thienyl -(2)- glyoxylic acid and thiosemicarbazide. By analagous methods are obtained 3-mercapto -1:2:4- triazine -5-(2H)-ones substituted in the 6-position by a -pyrryl-, a -pyridyl-, b -pyridyl-, quinaldyl, and 8-hydroxyquinolyl -(5)- radicals.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH705609X | 1950-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB705609A true GB705609A (en) | 1954-03-17 |
Family
ID=4530356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18061/51A Expired GB705609A (en) | 1950-08-01 | 1951-07-31 | Improvements in and relating to 1:2:4-triazine derivatives |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE860949C (en) |
| FR (1) | FR1040217A (en) |
| GB (1) | GB705609A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3139431A (en) * | 1960-02-23 | 1964-06-30 | Norwich Pharma Co | 6-(5-nitro-2-furyl) azauracil |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670912C3 (en) * | 1967-08-18 | 1981-06-11 | Bayer Ag, 5090 Leverkusen | Herbicidal agents based on 1,2,4-triazin-5-ones |
-
1951
- 1951-07-31 GB GB18061/51A patent/GB705609A/en not_active Expired
- 1951-07-31 FR FR1040217D patent/FR1040217A/en not_active Expired
- 1951-08-01 DE DEG6671A patent/DE860949C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3139431A (en) * | 1960-02-23 | 1964-06-30 | Norwich Pharma Co | 6-(5-nitro-2-furyl) azauracil |
Also Published As
| Publication number | Publication date |
|---|---|
| DE860949C (en) | 1952-12-29 |
| FR1040217A (en) | 1953-10-13 |
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