ES426206A1 - 2-aminothiazole derivatives - Google Patents
2-aminothiazole derivativesInfo
- Publication number
- ES426206A1 ES426206A1 ES426206A ES426206A ES426206A1 ES 426206 A1 ES426206 A1 ES 426206A1 ES 426206 A ES426206 A ES 426206A ES 426206 A ES426206 A ES 426206A ES 426206 A1 ES426206 A1 ES 426206A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- attached
- atom
- nitrogen
- hydrogen
- 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
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 title 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- -1 cycloalloxy Chemical group 0.000 abstract 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 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
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 150000007979 thiazole derivatives Chemical class 0.000 abstract 1
- 230000001052 transient effect Effects 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/18—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or 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
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Preparation procedure of derivatives of formula: ** (See formula) ** where E is a group of formula: ** (See formula) ** attached to the sulfur atom by its second carbon atom, R1 and R2, identical or different from each other, are hydrogen or radicals, optionally halogenated and/or hydroxylated, alkenyl, alkoxy, cycloalloxy, aryl, or arylalkyl, or form, together with the nitrogen atom to which they are attached, a saturated heterocycle with 4 to 8 rings, possibly having the second heteroatom, a nitrogen, sulfur or oxygen atom and possibly substituted by an alcohol, and R1 and R4, identical or different from each other, are hydrogen, alcoholic, or cycloalkyl, or form, together with the nitrogen atom to which they are attached, a saturated heterocycle of 5 or 6 rings, possibly having an oxygen or nitrogen heteroatom, being able The latter nitrogen heteroatom bears an aryl, optionally substituted by a halogen, by a trifluoromethyl or by an optionally halogenated and/or hydroxylated alcohol or alkoxy radical, characterized in that consists of reacting an amine AH on an isothiocyanate BN = C = S, where A is -H (R1-R2) when B is -CH2-RO-CH2-N (R3R4) and, with the proviso that R2 is hydrogen, where N (R3R4) -CH2-RO-CH2-NH- when B is R1-, where RO is the vinylene radical -CH = CH- or ethylene -C C-, to form the transient compound of formula: ** (See formula) ** then, by heating in an acidic medium, in cyclizing this transitory compound in the thiazolinic derivative of formula: ** (See formula) ** wherein R is the saturated trivalent radical, when RO is vinyl, or is the unsaturated trivalent radical attached to the nitrogen atom by its carbon atom not adjacent to its double bond, when RO is ethynylene, and, to prepare the thiazole derivative of formula (I) in which R is attached to the nitrogen atom by its carbon atom adjacent to its double bond to isomerize the derivative (Ia) in which R has a double bond. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7317698A FR2247234B1 (en) | 1973-05-16 | 1973-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES426206A1 true ES426206A1 (en) | 1976-07-01 |
Family
ID=9119403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES426206A Expired ES426206A1 (en) | 1973-05-16 | 1974-05-11 | 2-aminothiazole derivatives |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5030888A (en) |
| AT (1) | AT334894B (en) |
| BE (1) | BE814579A (en) |
| CA (1) | CA1057292A (en) |
| CH (1) | CH595364A5 (en) |
| DD (1) | DD112268A5 (en) |
| DE (1) | DE2423403A1 (en) |
| ES (1) | ES426206A1 (en) |
| FR (1) | FR2247234B1 (en) |
| GB (1) | GB1456257A (en) |
| HU (1) | HU169176B (en) |
| IL (1) | IL44845A (en) |
| NL (1) | NL7406490A (en) |
| PL (1) | PL91265B1 (en) |
| RO (1) | RO66055A (en) |
| SE (1) | SE429653B (en) |
| SU (1) | SU535906A3 (en) |
| YU (1) | YU36712B (en) |
| ZA (1) | ZA743048B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4018786A (en) * | 1974-08-06 | 1977-04-19 | Centre D'etudes Pour L'industrie Pharmaceutique | 2-Aminothiazolines and a process for preparation thereof |
| GB2550950B (en) * | 2016-06-02 | 2021-03-10 | Dixon Barnaby | Puppet |
-
1973
- 1973-05-16 RO RO7378803A patent/RO66055A/en unknown
- 1973-05-16 FR FR7317698A patent/FR2247234B1/fr not_active Expired
-
1974
- 1974-05-05 SU SU742027407A patent/SU535906A3/en active
- 1974-05-06 BE BE143945A patent/BE814579A/en not_active IP Right Cessation
- 1974-05-11 ES ES426206A patent/ES426206A1/en not_active Expired
- 1974-05-13 ZA ZA00743048A patent/ZA743048B/en unknown
- 1974-05-14 DE DE2423403A patent/DE2423403A1/en not_active Withdrawn
- 1974-05-14 DD DD178502A patent/DD112268A5/xx unknown
- 1974-05-15 SE SE7406478A patent/SE429653B/en unknown
- 1974-05-15 YU YU1332/74A patent/YU36712B/en unknown
- 1974-05-15 GB GB2161474A patent/GB1456257A/en not_active Expired
- 1974-05-15 NL NL7406490A patent/NL7406490A/xx not_active Application Discontinuation
- 1974-05-15 CA CA199,994A patent/CA1057292A/en not_active Expired
- 1974-05-15 CH CH665274A patent/CH595364A5/xx not_active IP Right Cessation
- 1974-05-15 HU HUCE999A patent/HU169176B/hu unknown
- 1974-05-15 AT AT403574A patent/AT334894B/en not_active IP Right Cessation
- 1974-05-16 PL PL1974171105A patent/PL91265B1/pl unknown
- 1974-05-16 JP JP49053961A patent/JPS5030888A/ja active Pending
- 1974-05-16 IL IL44845A patent/IL44845A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU169176B (en) | 1976-10-28 |
| CA1057292A (en) | 1979-06-26 |
| IL44845A0 (en) | 1974-07-31 |
| FR2247234A1 (en) | 1975-05-09 |
| IL44845A (en) | 1977-06-30 |
| GB1456257A (en) | 1976-11-24 |
| RO66055A (en) | 1981-07-30 |
| AU6889574A (en) | 1975-11-20 |
| AT334894B (en) | 1977-02-10 |
| SU535906A3 (en) | 1976-11-15 |
| JPS5030888A (en) | 1975-03-27 |
| FR2247234B1 (en) | 1977-01-21 |
| ATA403574A (en) | 1976-06-15 |
| CH595364A5 (en) | 1978-02-15 |
| SE429653B (en) | 1983-09-19 |
| NL7406490A (en) | 1974-11-19 |
| DD112268A5 (en) | 1975-04-05 |
| BE814579A (en) | 1974-09-02 |
| YU36712B (en) | 1984-08-31 |
| ZA743048B (en) | 1975-05-28 |
| YU133274A (en) | 1982-06-18 |
| DE2423403A1 (en) | 1974-12-05 |
| PL91265B1 (en) | 1977-02-28 |
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