AU2997689A - Process for the preparation of thiophene derivatives and also new dihydrothiophene 1-oxides - Google Patents
Process for the preparation of thiophene derivatives and also new dihydrothiophene 1-oxidesInfo
- Publication number
- AU2997689A AU2997689A AU29976/89A AU2997689A AU2997689A AU 2997689 A AU2997689 A AU 2997689A AU 29976/89 A AU29976/89 A AU 29976/89A AU 2997689 A AU2997689 A AU 2997689A AU 2997689 A AU2997689 A AU 2997689A
- Authority
- AU
- Australia
- Prior art keywords
- thiophene derivatives
- dihydrothiophene
- oxides
- preparation
- new
- 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.)
- Granted
Links
- 150000003577 thiophenes Chemical class 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 2
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 239000011814 protection agent Substances 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
- C07D333/48—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Thiophene derivatives with an optionally substituted amino group on the thiophene ring are prepared by dehydrogenation of dihydrothiophenes which are substituted in the same manner as the desired thiophene derivatives, using H2O2, the dihydrothiophenes being reacted in a first reaction step with H2O2 in neutral medium to give the corresponding sulphoxides, and, in the second reaction step, these are then rearranged with acid to give the thiophene derivatives. The dihydrothiophene-1-oxides which are formed in this process as intermediates are novel compounds. They, and equally the thiophene derivatives obtained from them by rearrangement with acid, are intermediates mainly in the crop protection agent sector and pharmaceutical sector.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3804794 | 1988-02-16 | ||
DE3804794A DE3804794A1 (en) | 1988-02-16 | 1988-02-16 | METHOD FOR PRODUCING THIOPHENE DERIVATIVES AND NEW DIHYDROTHIOPHEN-1-OXIDES |
Publications (2)
Publication Number | Publication Date |
---|---|
AU2997689A true AU2997689A (en) | 1989-08-17 |
AU612788B2 AU612788B2 (en) | 1991-07-18 |
Family
ID=6347511
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU29976/89A Expired AU612788B2 (en) | 1988-02-16 | 1989-02-15 | Process for the preparation of thiophene derivatives and also new dihydrothiophene 1-oxides |
Country Status (12)
Country | Link |
---|---|
EP (1) | EP0331919B1 (en) |
JP (1) | JP2721695B2 (en) |
KR (1) | KR960014799B1 (en) |
AT (1) | ATE92483T1 (en) |
AU (1) | AU612788B2 (en) |
CA (1) | CA1338108C (en) |
DE (2) | DE3804794A1 (en) |
DK (1) | DK173888B1 (en) |
ES (1) | ES2059585T3 (en) |
IE (1) | IE63074B1 (en) |
PT (1) | PT89717B (en) |
ZA (1) | ZA891163B (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2917979A (en) * | 1956-02-27 | 1959-12-22 | Garlinghouse Brothers | Compactor |
DE4134755A1 (en) * | 1991-10-22 | 1993-04-29 | Bayer Ag | USE OF PARTLY KNOWN SUBSTITUTED TETRAHYDROTHIOPHENES AS A MEDICINAL PRODUCT, NEW ACTIVE SUBSTANCES AND METHOD FOR THE PRODUCTION THEREOF |
FR2858323A1 (en) * | 2003-07-28 | 2005-02-04 | Oreal | New derivatives of 3-amino-4,5-dihydrothiophene and their use in cosmetic compositions to lighten and brighten the skin, prevent browning and remove brown patches such as age spots |
DE102004063191A1 (en) * | 2004-12-29 | 2006-07-13 | Bayer Cropscience Ag | Process for the preparation of substituted 2-alkoxycarbonyl-3-aminothiophenes |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2700215A1 (en) * | 1977-01-05 | 1978-07-13 | Basf Ag | Substd. thiophenes prepn. by dehydrogenation - of dihydrothiophenes or disulphido-bis-dihydrothiophenes, using halogen (cpds.) |
US4596595A (en) * | 1984-06-22 | 1986-06-24 | Chevron Research Company | Herbicidal 5-amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrothiophene and derivatives thereof |
GB2194530A (en) * | 1986-09-02 | 1988-03-09 | Shell Int Research | Diphenyl ether compounds |
-
1988
- 1988-02-16 DE DE3804794A patent/DE3804794A1/en not_active Withdrawn
-
1989
- 1989-02-09 DE DE8989102212T patent/DE58905083D1/en not_active Expired - Lifetime
- 1989-02-09 ES ES89102212T patent/ES2059585T3/en not_active Expired - Lifetime
- 1989-02-09 AT AT89102212T patent/ATE92483T1/en not_active IP Right Cessation
- 1989-02-09 EP EP89102212A patent/EP0331919B1/en not_active Expired - Lifetime
- 1989-02-14 IE IE483889A patent/IE63074B1/en not_active IP Right Cessation
- 1989-02-15 ZA ZA891163A patent/ZA891163B/en unknown
- 1989-02-15 JP JP1033894A patent/JP2721695B2/en not_active Expired - Lifetime
- 1989-02-15 CA CA000591117A patent/CA1338108C/en not_active Expired - Lifetime
- 1989-02-15 DK DK198900695A patent/DK173888B1/en not_active IP Right Cessation
- 1989-02-15 AU AU29976/89A patent/AU612788B2/en not_active Expired
- 1989-02-15 PT PT89717A patent/PT89717B/en not_active IP Right Cessation
- 1989-02-15 KR KR89001709A patent/KR960014799B1/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
KR960014799B1 (en) | 1996-10-19 |
KR890012993A (en) | 1989-09-20 |
PT89717B (en) | 1994-03-31 |
ATE92483T1 (en) | 1993-08-15 |
DK69589D0 (en) | 1989-02-15 |
JP2721695B2 (en) | 1998-03-04 |
CA1338108C (en) | 1996-03-05 |
DK69589A (en) | 1989-08-17 |
DE58905083D1 (en) | 1993-09-09 |
EP0331919A2 (en) | 1989-09-13 |
AU612788B2 (en) | 1991-07-18 |
DE3804794A1 (en) | 1989-08-24 |
ES2059585T3 (en) | 1994-11-16 |
IE63074B1 (en) | 1995-03-22 |
DK173888B1 (en) | 2002-01-28 |
ZA891163B (en) | 1989-10-25 |
EP0331919B1 (en) | 1993-08-04 |
EP0331919A3 (en) | 1989-10-18 |
JPH01249766A (en) | 1989-10-05 |
PT89717A (en) | 1989-10-04 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PC | Assignment registered |
Owner name: AVENTIS PHARMA DEUTSCHLAND GMBH Free format text: FORMER OWNER WAS: HOECHST AKTIENGESELLSCHAFT |