ES431268A1 - A procedure for preparing tiaol derivatives. (Machine-translation by Google Translate, not legally binding) - Google Patents
A procedure for preparing tiaol derivatives. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES431268A1 ES431268A1 ES74431268A ES431268A ES431268A1 ES 431268 A1 ES431268 A1 ES 431268A1 ES 74431268 A ES74431268 A ES 74431268A ES 431268 A ES431268 A ES 431268A ES 431268 A1 ES431268 A1 ES 431268A1
- Authority
- ES
- Spain
- Prior art keywords
- general formula
- ring
- cycloalkoxylalkyl
- 5alkynyl
- 5alkenyl
- 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
- 238000000034 method Methods 0.000 title abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 150000002367 halogens Chemical class 0.000 abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 230000007062 hydrolysis Effects 0.000 abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- -1 alkoxy alcohol Chemical compound 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 239000011593 sulfur Substances 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- KVLCHQHEQROXGN-UHFFFAOYSA-N aluminium(1+) Chemical compound [Al+] KVLCHQHEQROXGN-UHFFFAOYSA-N 0.000 abstract 1
- 229940007076 aluminum cation Drugs 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
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 229940116906 cupric cation Drugs 0.000 abstract 1
- 238000007333 cyanation reaction Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 150000007979 thiazole derivatives Chemical class 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
-
- 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
- C07D277/34—Oxygen 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
- C07D277/36—Sulfur 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
- C07D277/42—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
- C07D277/20—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
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
A procedure for preparing thiazole derivatives of the general formula: **(See formula)** wherein A is oxygen, sulfur, imino, or NR3; R3 is C1-5alkyl, C1-5alkenyl, C3-5alkynyl, cycloalkoxylalkyl or C3-6alkyl; R1 is hydrogen, C1-5alkyl, C1-5alkenyl, C3-5alkynyl, cycloalkoxylalkyl or aralcoyl; R2 is hydroxy, an ester residue or OM; M is an alkali metal, an equivalent of an alkaline earth metal, the cupric or aluminum cation; n is an integer from 0 or 1 and the thiazole ring can have one or two substituents selected from C1-5 alcohol or halogen and the benzene ring can have one or two substituents selected from halogen, C1-5 alkoxy alcohol of C1-5 or trifluoromethyl, comprising: (A) condensing a compound represented by the general formula [IIa] or [IIb]: **(See formula)** where hal is chlorine, bromine or iodine and Z is a group that can become (see formula) by hydrolysis; R1 is hydrogen, C1-5alkyl, and C1-5alkenyl, C3-5alkynyl, cycloalkoxylalkyl or C3-6alkyl and the thiazole ring may have one or two substances selected from C1-5alcoyl, or Halogen and the benzene ring may have one or two substituents selected from halogen, C1-5 alcohol, C1-5 alkoxy or trifluoromethyl, with a phenyl compound represented by the general formula [IIIa] or [IIIb] respectively: **(See formula)** where A is oxygen, sulfur, imino or NR3; R3 is C1-5alkyl, C1-5alkenyl, C3-5alkynyl, cycloalkoxylalkyl or C3-6alralkoyl, Z has the same meaning as designated above and the benzene ring may have one or two substituents selected from halogen, alcoholic C1-5, C1-5 alkoxy or trifluoromethyl; and, if necessary, further subjecting hydrolysis or (B) subjecting cyanation (1) a compound represented by the general formula [IV]: **(See formula)** wherein hal, A and n have the same meanings as above and the thiazole ring and the benzene ring may have the above named substituents and (2) then hydrolyze with or without esterification to obtain a compound represented by the general formula [VI] : **(See formula)** where W is hydroxy or an ester residue; A and n have the same meanings as designated above and the benzene ring and the thiazole ring may have the above named substituents or (3) condensation with a halogenated hydrocarbon before or after the above hydrolysis, if necessary, to obtain a compound represented by the general formula [I']: **(See formula)** wherein R'1 is C5-5alkyl, C1-5alkenyl, C3-5alkynyl, and cycloalkoxylalkyl or aralkoxy is C3-6, A and W each have the same meanings as designated above and the ring The benzene and thiazole ring may have the substituents designated above, and also undergo a procedure to obtain their salts, if necessary. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11958373A JPS565747B2 (en) | 1973-10-24 | 1973-10-24 | |
| JP12153473A JPS5742629B2 (en) | 1973-10-29 | 1973-10-29 | |
| JP24774A JPS5537556B2 (en) | 1973-12-27 | 1973-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES431268A1 true ES431268A1 (en) | 1976-11-01 |
Family
ID=27274373
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES74431268A Expired ES431268A1 (en) | 1973-10-24 | 1974-10-23 | A procedure for preparing tiaol derivatives. (Machine-translation by Google Translate, not legally binding) |
| ES76448671A Expired ES448671A1 (en) | 1973-10-24 | 1976-06-08 | A procedure for preparing tiazol derivatives. (Machine-translation by Google Translate, not legally binding) |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES76448671A Expired ES448671A1 (en) | 1973-10-24 | 1976-06-08 | A procedure for preparing tiazol derivatives. (Machine-translation by Google Translate, not legally binding) |
Country Status (4)
| Country | Link |
|---|---|
| CH (2) | CH617686A5 (en) |
| ES (2) | ES431268A1 (en) |
| NL (1) | NL179818C (en) |
| SE (1) | SE431453B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5879440A (en) * | 1997-07-28 | 1999-03-09 | Hercules Incorporated | Biostable water-borne paints and processes for their preparation |
-
1974
- 1974-10-23 ES ES74431268A patent/ES431268A1/en not_active Expired
- 1974-10-23 CH CH1025778A patent/CH617686A5/en not_active IP Right Cessation
- 1974-10-23 SE SE7413333A patent/SE431453B/en not_active IP Right Cessation
- 1974-10-23 CH CH1420074A patent/CH613199A5/en not_active IP Right Cessation
- 1974-10-24 NL NLAANVRAGE7413927,A patent/NL179818C/en not_active IP Right Cessation
-
1976
- 1976-06-08 ES ES76448671A patent/ES448671A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL179818C (en) | 1986-11-17 |
| CH617686A5 (en) | 1980-06-13 |
| NL7413927A (en) | 1975-04-28 |
| SE431453B (en) | 1984-02-06 |
| SE7413333L (en) | 1975-04-25 |
| NL179818B (en) | 1986-06-16 |
| ES448671A1 (en) | 1977-07-01 |
| CH613199A5 (en) | 1979-09-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SE8401134D0 (en) | PROCEDURE FOR THE PREPARATION OF DIHYDRO-CYCLOSPORIN D | |
| SE8005534L (en) | QUINOLINE CARBOXYLIC ACID DERIVATIVES AND SETS FOR PREPARING THEREOF | |
| ES481220A1 (en) | Novel Aminothiazoles | |
| ES369005A1 (en) | Alpha-amino-cyclohexadienylalkylene-penicillins and cephalosporins | |
| ES427859A1 (en) | Antibiotics | |
| ES444398A1 (en) | 16,17,18,19,20-pentanorprostaglandins | |
| ES8305298A1 (en) | Analgesic and anti-inflammatory agents. | |
| ES432952A1 (en) | PROCEDURE TO PREPARE VINCAMINE DERIVATIVE. | |
| ES412587A1 (en) | Bicyclic nitrogenous compounds and salts | |
| ES404592A1 (en) | 2,3-dihydro-oxo-imidazo(1,2-a)pyrimidines and salts thereof | |
| NO854677L (en) | PROCEDURE FOR THE PREPARATION OF 5-ALKYL-1-PHENYL-2-PIPERAZINOALKYLPYRAZOLIN-3-ON COMPOUNDS. | |
| DK305879A (en) | R PROCEDURE FOR THE PREPARATION OF OXADIAZOLPYRIMIDINE DERIVATIVES | |
| ES431268A1 (en) | A procedure for preparing tiaol derivatives. (Machine-translation by Google Translate, not legally binding) | |
| GB1186495A (en) | 0-[3-(4-Fluorobenzoyl) Proplyl]-4-Substituted Piperazines, their Acid Addition Salts and their method of preparation | |
| SE8301785L (en) | SET TO MAKE 2-THIOPHENIC ACETIC ACID DERIVATIVES AND INTERMEDIATES REQUIRED FOR THEIR PREPARATION | |
| GB1352089A (en) | Bis-styryltriazoles their use for the optical brightening of organic materials and processes for their manufacture | |
| ES383683A1 (en) | Coumarin derivatives and their use as optical brighteners | |
| GB1076203A (en) | Cyclohepta-[b]-pyrrole derivatives | |
| SE7909157L (en) | PROCEDURE FOR THE PREPARATION OF CYCLE-1,3,2-OXAZAPHOSPHORPHYL DERIVATIVES | |
| ES421810A1 (en) | Pyrimidopyrimidines | |
| ES390275A1 (en) | A procedure for the preparation of 1,2-dialquil (lower) pirrolydines. (Machine-translation by Google Translate, not legally binding) | |
| GB677264A (en) | Improvements in and relating to stabilisers for photographic emulsions | |
| ES402471A1 (en) | A PROCEDURE FOR THE PREPARATION OF DERIVATIVES OF 1-ARI-LOXI-3-AMINO-PROPANOL. | |
| ATE255T1 (en) | SUBSTITUTED PHENYLPROPYLHALOGENIDES, THEIR PRODUCTION AND USE. | |
| ES439051A1 (en) | Procedure for the obtaining of new derivatives of diazepine. (Machine-translation by Google Translate, not legally binding) |