GB2008570A - The preparation of thiophene 2- and 3-malonic and acetic acids and esters - Google Patents
The preparation of thiophene 2- and 3-malonic and acetic acids and estersInfo
- Publication number
- GB2008570A GB2008570A GB7834389A GB7834389A GB2008570A GB 2008570 A GB2008570 A GB 2008570A GB 7834389 A GB7834389 A GB 7834389A GB 7834389 A GB7834389 A GB 7834389A GB 2008570 A GB2008570 A GB 2008570A
- Authority
- GB
- United Kingdom
- Prior art keywords
- thiophene
- malonic
- esters
- acetic acids
- preparation
- 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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title abstract 6
- 229930192474 thiophene Natural products 0.000 title abstract 3
- 235000011054 acetic acid Nutrition 0.000 title abstract 2
- 150000001243 acetic acids Chemical class 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title abstract 2
- 235000019439 ethyl acetate Nutrition 0.000 title abstract 2
- 238000000034 method Methods 0.000 abstract 3
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-O Thiophenium Chemical compound [SH+]1C=CC=C1 YTPLMLYBLZKORZ-UHFFFAOYSA-O 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229940124587 cephalosporin Drugs 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- -1 rhodium (II) carboxylate Chemical class 0.000 abstract 1
- 238000003786 synthesis reaction Methods 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
- C07D333/06—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by 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)
- Catalysts (AREA)
Abstract
Thiophene 2- and 3-malonic and acetic acids and esters are made by reacting a thiophene or a derivative thereof with a diazo compound in the presence, as catalyst, of a rhodium (II) carboxylate. The process may be a one stage process, or a two stage process via thiophenium ylid or a cyclopropane derivative as an intermediate compound. The product is useful in the synthesis of penicillin and cephalosporin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7834389A GB2008570B (en) | 1977-05-27 | 1978-08-24 | Preparation of 2-and3-substituted thiophene derivatives |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2262577 | 1977-05-27 | ||
| GB7834389A GB2008570B (en) | 1977-05-27 | 1978-08-24 | Preparation of 2-and3-substituted thiophene derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2008570A true GB2008570A (en) | 1979-06-06 |
| GB2008570B GB2008570B (en) | 1982-02-03 |
Family
ID=26256033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7834389A Expired GB2008570B (en) | 1977-05-27 | 1978-08-24 | Preparation of 2-and3-substituted thiophene derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2008570B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007006724A1 (en) * | 2005-07-13 | 2007-01-18 | Basf Aktiengesellschaft | 5-alkyl-7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine compounds and use thereof for the prevention of fungal pests |
-
1978
- 1978-08-24 GB GB7834389A patent/GB2008570B/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007006724A1 (en) * | 2005-07-13 | 2007-01-18 | Basf Aktiengesellschaft | 5-alkyl-7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine compounds and use thereof for the prevention of fungal pests |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2008570B (en) | 1982-02-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |