DD287033A5 - PROCESS FOR THE PREPARATION OF 2-ALKOXY-4-OXO-CHINAZOLIN-3-YL-ALKANSAURES - Google Patents
PROCESS FOR THE PREPARATION OF 2-ALKOXY-4-OXO-CHINAZOLIN-3-YL-ALKANSAURES Download PDFInfo
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- DD287033A5 DD287033A5 DD33185989A DD33185989A DD287033A5 DD 287033 A5 DD287033 A5 DD 287033A5 DD 33185989 A DD33185989 A DD 33185989A DD 33185989 A DD33185989 A DD 33185989A DD 287033 A5 DD287033 A5 DD 287033A5
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Abstract
Die Erfindung betrifft ein Verfahren zur Herstellung von 2-Alkoxy-4-oxo-chinazolin-3-yl-alkansaeuren. Erfindungsgemaesz wird ein * in einem aliphatischen primaeren Alkohol mit einem Alkalihydroxid unter Erwaermen zu einer * der allgemeinen Formel II umgesetzt. Unter den Verbindungen der allgemeinen Formel II befinden sich fungizid oder pflanzenwachstumsregulatorisch wirksame Substanzen. Formel II{* *}The invention relates to a process for the preparation of 2-alkoxy-4-oxo-quinazolin-3-yl-alkan acids. According to the present invention, an * in an aliphatic primary alcohol is reacted with an alkali hydroxide while being heated to * of the general formula II. Among the compounds of general formula II are fungicidal or plant growth regulatory substances. Formula II {* *}
Description
Anwendungsgebiet der ErfindungField of application of the invention
Die Erfindung betrifft ein Verfahren zur Herstellung von 2-Alkoxy-4-oxo-chinazolln-3-yl-alkansäuren der allgemeinen Fo/mel Die Erfindung is' für die Land-, Garten- und Forstwirtschaft von Interesse, wo erfindungsgemäß hergestellte Verbindungen z. B. als Fungizide oder Pflanzenwachstumsregulatoren einsetzbar sind.The invention relates to a process for the preparation of 2-alkoxy-4-oxo-quinazolln-3-yl-alkanoic acids of the general formula The invention is' for the agriculture, horticulture and forestry of interest, where compounds prepared according to the invention z. B. can be used as fungicides or plant growth regulators.
Eine große Anzahl von Chinazolinen mit potentieller Wirkung als Phytoeffektoren, Fungizide, Akarizide, Insektizide oder Herbizide ist bekannt (M. Süße, S.Johne, Z. Chem. 21,431 [1981]).A large number of quinazolines with potential action as phyto-effectors, fungicides, acaricides, insecticides or herbicides are known (Süße, S.Johne, Z. Chem., 21, 431 [1981]).
Einige 4-Alkoxy- und 2,4-Dialkoxy-chinazoline wurden bisher aus den entsprechenden Halogenchinazolinen und Alkoholaten erhalten (W. L. F. Armarego, „The Chemistry of Heterocyclic Compounds", 24. Band «Fused Pyrimidines, I. Quinazolines", New York, London, Sydney, (19671).Some 4-alkoxy- and 2,4-dialkoxy-quinazolines have hitherto been obtained from the corresponding haloquinazolines and alcoholates (WLF Armarego, "The Chemistry of Heterocyclic Compounds", 24th volume "Fused Pyrimidines, I. Quinazolines", New York, London , Sydney, (19671).
2-Alkoxy-4-oxo-chinazolin-3-yl-alksnsäuren der allgemeinen Formel Il sind bisher nicht bekannt.2-alkoxy-4-oxo-quinazolin-3-yl-alksnsäuren the general formula II are not yet known.
Ziel der ErfindungObject of the invention
Ziel der Erfindung ist es, neue, biologisch aktive 2-Alkoxy-4-oxo-chinazolin-3-yl-alkunsäuren der Praxis als Wirkstoffe zur Verfügung zu stellen.The aim of the invention is to provide new, biologically active 2-alkoxy-4-oxo-quinazolin-3-yl-alkunsäuren the practice as active ingredients available.
Darlegung des Wesens der ErfindungExplanation of the essence of the invention
Die Aufgabe der Erfindung besteht darin, ein Verfahren zur Herstellung von 2-Alkoxy-4-oxo-chinazolin-3-yl-alkansäuren der allgemeinen Formel Il zu entwickeln.The object of the invention is to develop a process for the preparation of 2-alkoxy-4-oxo-quinazolin-3-yl-alkanoic acids of the general formula II.
Erfindungsgemäß wird ein 2-Alkylthio-3,4-dihydro-4-oxo-chinazolin-3-yl-alkansäureester der allgemeinen Formel I in einem aliphatischen primären Alkohol mit einem Alkalihydroxid unter Erwärmen zu einer 2-Aikoxy-3,4-dihydro-4-oxo-chinazolin-3-ylalkansäure der allgemeinen Formel 11 umgesetzt.According to the invention, a 2-alkylthio-3,4-dihydro-4-oxo-quinazolin-3-yl-alkanoic acid ester of general formula I in an aliphatic primary alcohol with an alkali metal hydroxide is heated to a 2-aikoxy-3,4-dihydroxy 4-oxo-quinazolin-3-ylalkanoic acid of general formula 11 implemented.
Überraschenderweise findet unter diesen Reaktionsbedingungen neben der Hydrolyse der Estergruppe (-COOR2) eine Substitution der Alkylthiogruppe (-SR) statt.Surprisingly, in addition to the hydrolysis of the ester group (-COOR 2 ), a substitution of the alkylthio group (-SR) takes place under these reaction conditions.
In den allgemeinen Formeln I und Il stehen R, R2 und R3 (vorzugsweise C)-C4, gleich oder verschieden) für Alkyl, X für Alkylen (geradkettig IC1-C10] oder verzweigt, gegebenenfalls substituiert), R1 für Alkyl, Alkoxy, Halogen, CF3, NO2, CN oder Dialkylamino und η für O bis -Ϊ, wobei in den Fällen η = 2,3 oder 4 die R' gleich oder verschieden sind.In general formulas I and II, R, R 2 and R 3 (preferably C) -C 4 , same or different) are alkyl, X is alkylene (straight chain IC 1 -C 10 ] or branched, optionally substituted), R 1 for alkyl, alkoxy, halogen, CF 3 , NO 2 , CN or dialkylamino and η for O to -Ϊ, where in the cases η = 2,3 or 4, the R 'are the same or different.
Das erfindungsgemäße Verfahren ermöglicht erstmalig die Herstellung der Verbindungen der allgemeinen Formel II.The process according to the invention makes it possible for the first time to prepare the compounds of the general formula II.
Die Verbindungen der allgemeinen Formel Il sind biologisch aktiv. Unter ihnen befinden sich solche, die eine fungizide oder pflanzenwachstumsregulatorische Wirkung zeigen.The compounds of general formula II are biologically active. Among them are those which have a fungicidal or plant growth regulatory effect.
Die Erfindung wird nachstehend durch Ausführungsbeispiele erlüutert.The invention will be explained below by embodiments.
Ausführungsbeispieleembodiments
300mg S^-Dihydro^-methylthio^-oxo-chinazolin-S-yl-essigsäuremethylester (I: η = 0, R = R2 = CH3, X = CH2) und 240mg KOH werden in 30ml 95%igem Methanol 1 Stunde unter Rückfluß erhitzt. Das Methanol wird im Vakuum abdestilliert und der Rückstand aus Ethanol mit Aktivkohle umkristallisiert; Ausbeute: 160mg an S^- essigsäure (II: η = 0, R3 = CH3, X = CH2).300 mg of methyl S ^ -dihydro-methylthio ^ -oxo-quinazolin-S-yl acetate (I: η = 0, R = R 2 = CH 3 , X = CH 2 ) and 240 mg of KOH are dissolved in 30 ml of 95% methanol 1 Heated under reflux for one hour. The methanol is distilled off in vacuo and the residue recrystallized from ethanol with activated charcoal; Yield: 160 mg of S - acetic acid (II: η = 0, R 3 = CH 3 , X = CH 2 ).
-J--J-
Λ8ΨΟΜΛ8ΨΟΜ
N-X-COOR2 NX COOR 2
g-X-COOHg-X-COOH
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD33185989A DD287033A5 (en) | 1989-08-17 | 1989-08-17 | PROCESS FOR THE PREPARATION OF 2-ALKOXY-4-OXO-CHINAZOLIN-3-YL-ALKANSAURES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD33185989A DD287033A5 (en) | 1989-08-17 | 1989-08-17 | PROCESS FOR THE PREPARATION OF 2-ALKOXY-4-OXO-CHINAZOLIN-3-YL-ALKANSAURES |
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| Publication Number | Publication Date |
|---|---|
| DD287033A5 true DD287033A5 (en) | 1991-02-14 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD33185989A DD287033A5 (en) | 1989-08-17 | 1989-08-17 | PROCESS FOR THE PREPARATION OF 2-ALKOXY-4-OXO-CHINAZOLIN-3-YL-ALKANSAURES |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994026722A1 (en) * | 1993-05-12 | 1994-11-24 | E.I. Du Pont De Nemours And Company | Fungicidal fused bicyclic pyrimidinones |
-
1989
- 1989-08-17 DD DD33185989A patent/DD287033A5/en not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994026722A1 (en) * | 1993-05-12 | 1994-11-24 | E.I. Du Pont De Nemours And Company | Fungicidal fused bicyclic pyrimidinones |
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