GB1049031A - Malonic acid derivatives - Google Patents
Malonic acid derivativesInfo
- Publication number
- GB1049031A GB1049031A GB714764A GB714764A GB1049031A GB 1049031 A GB1049031 A GB 1049031A GB 714764 A GB714764 A GB 714764A GB 714764 A GB714764 A GB 714764A GB 1049031 A GB1049031 A GB 1049031A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- acids
- diethyl
- alkoxy
- pyrone
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention comprises allylidenemalonic acid compounds of formula <FORM:1049031/C2/1> where R and R1 represent hydrogen or alkyl radicals, R2 an alkoxy or -NHR4 where R4 represents hydrogen or an alkyl, aryl or aralkyl radical, specifically diethyl esters of 3(C1-C5) alkoxy allylidene malonic acids, 3-aminoallylidenemalonic acid, diethyl-3-amino-allylidencemalonate, 3-alkylaminoallylidene-malonic acids and their diethyl esters. The 3-alkoxy-allylidene-malonic acid compound is prepared by reacting in the presence of a Lewis acid a tetraalkoxypropane of formula <FORM:1049031/C2/2> with malonic acid or an alkyl ester thereof, and the 3-amino acids are prepared by a further reaction with ammonia, a primary alkylamine, arylamine or aralkylamine. The alkoxy acids may be cyclized by heating in the presence of a strong acid to produce a -pyrone-3-carboxylic acids, and the amino-acids may be cyclized with a base to yield a -pyridone-3-carboxylic acid. Examples describe the preparation of diethylethoxyallylidenemalonate, 3 - ethoxyallylidenemalonic acid, diethyl-3-aminoallylidenemalonate, diethyl - 3 - benzylaminoallylidene malonate, ethyl - a - pyrone - 3 - carboxylate, a - pyrone - 3 - carboxylic acid, ethyland ethyl - N - benzyl - a - pyridone - 3 - carbxylate and N - benzyl - a - pyridone - 3 - carboxylic acid. The alkoxyallylidene diethyl malonate may be reacted with urea in the presence of sodium methoxide to form 5-(alkoxy - aminoallylidene) barbituric acid and equal molar amounts of 6-aminopenicillanic acid and a -pyrone-3-carboxylic acid reacted in the presence of dicyclohexyl-carbodiimide forms a penicillin of formula <FORM:1049031/C2/3>
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26310963A | 1963-03-06 | 1963-03-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1049031A true GB1049031A (en) | 1966-11-23 |
Family
ID=23000404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB714764A Expired GB1049031A (en) | 1963-03-06 | 1964-02-20 | Malonic acid derivatives |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1468312A1 (en) |
| GB (1) | GB1049031A (en) |
| NL (1) | NL6402325A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986001202A1 (en) * | 1984-08-03 | 1986-02-27 | American Hospital Supply Corporation | Pyridone esters as inotropic agents |
| CN117658900A (en) * | 2022-08-30 | 2024-03-08 | 南京药石科技股份有限公司 | A kind of preparation method of tetrahydronaphthyridine compounds and its intermediates |
-
1964
- 1964-02-20 GB GB714764A patent/GB1049031A/en not_active Expired
- 1964-03-04 DE DE19641468312 patent/DE1468312A1/en active Pending
- 1964-03-06 NL NL6402325A patent/NL6402325A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986001202A1 (en) * | 1984-08-03 | 1986-02-27 | American Hospital Supply Corporation | Pyridone esters as inotropic agents |
| CN117658900A (en) * | 2022-08-30 | 2024-03-08 | 南京药石科技股份有限公司 | A kind of preparation method of tetrahydronaphthyridine compounds and its intermediates |
| CN117658900B (en) * | 2022-08-30 | 2025-11-21 | 南京药石科技股份有限公司 | Preparation method of tetrahydronaphthyridine compound and intermediate thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1468312A1 (en) | 1968-11-28 |
| NL6402325A (en) | 1964-09-07 |
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