DD249475A1 - PROCESS FOR THE PREPARATION OF 2,3,4,5-TETRAHYDRO-2,5-DIOXO-1H-1,4-BENZODIAZEPINE-3-CARBOXYLIC ACID ESTERS - Google Patents
PROCESS FOR THE PREPARATION OF 2,3,4,5-TETRAHYDRO-2,5-DIOXO-1H-1,4-BENZODIAZEPINE-3-CARBOXYLIC ACID ESTERS Download PDFInfo
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- DD249475A1 DD249475A1 DD29069286A DD29069286A DD249475A1 DD 249475 A1 DD249475 A1 DD 249475A1 DD 29069286 A DD29069286 A DD 29069286A DD 29069286 A DD29069286 A DD 29069286A DD 249475 A1 DD249475 A1 DD 249475A1
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- benzodiazepine
- dioxo
- carboxylic acid
- acid esters
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Abstract
Ziel der Erfindung ist es, biologisch aktive 2,5-Dioxo-1,4-benzodiazepin-3-carbonsaeureester der Praxis als Wirkstoffe zur Verfuegung zu stellen. Erfindungsgemaess wird ein Isatosaeureanhydrid der allgemeinen Formel I in Loesung oder Suspension in einem dipolar-aprotischen Loesungsmittel unter Erwaermen mit einem Aminomalonsaeureester der allgemeinen Formel II zur entsprechenden Verbindung der allgemeinen Formel III umgesetzt. Unter den Verbindungen der allgemeinen Formel III befinden sich fungizid und/oder pflanzenwachstumsregulatorisch wirksame Substanzen.The aim of the invention is to provide biologically active 2,5-dioxo-1,4-benzodiazepine-3-carboxylic acid esters as active ingredients in the practice. According to the invention, an isatoic anhydride of the general formula I in solution or suspension in a dipolar aprotic solvent is reacted with an aminomalonic ester of the general formula II to give the corresponding compound of the general formula III. Among the compounds of general formula III are fungicidal and / or plant growth regulatory substances.
Description
Hierzu 1 Seite FormelnFor this 1 page formulas
Die Erfindung betrifft ein Verfahren zur Herstellung von 2,3,4,5-Tetrahydro-2,5*dioxo-1H-1,4-benzodiazepin-3-carbonsäureestern der allgemeinen Formel III.The invention relates to a process for the preparation of 2,3,4,5-tetrahydro-2,5 * dioxo-1H-1,4-benzodiazepine-3-carboxylic acid esters of the general formula III.
Anwendungsgebiet der ErfindungField of application of the invention
Die Erfindung ist für Land-, Garten- und Forstwirtschaft von Interesse, wo erfindungsgemä'ß hergestellte Verbindungen^. B. als Fungizide oder als Pflanzenwachstumsregulatore^einsetzbar sind.The invention is of interest for agriculture, horticulture and forestry, where erfindungsgemä'ß compounds produced ^. B. as fungicides or as Pflanzenwachstumsregulatore ^ can be used.
Charakteristik der bekannten technischen LösungenCharacteristic of the known technical solutions
Hydrierte 2H-Azepin-2-one und Nitro-triazepine zeigen starke herbizide Eigenschaften (R. Wegler: Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel, Bd. 5, Berlin, Heidelberg, New York, Springer-Verlag 1977).Hydrogenated 2H-azepin-2-ones and nitro-triazepines show strong herbicidal properties (R. Wegler: Chemie der Pflanzenschutz- und Schädlingsbekungsmittel, Bd. 5, Berlin, Heidelberg, New York, Springer-Verlag 1977).
1,4-Benzodiazepin-2,5-dione wurden durch Reaktion von Isatosäureanhydriden mit Glycinester in Pyridin (G. M. Coppola, Synthesis 1980,505; D. H. Kim, J. Heterocycl. Chem. 12,1323(1975]) oder mit Glycin in Essigsäure (M. Gates, J. Org. Chem. 45, 1675[198O]) unter Rückfluß erhalten. Diese Verfahren führen jedoch nicht zu Verbindungen, die in 3-Stellung funktioneile Gruppen enthalten. 2,3,4,5-Tetrahydro-2,5-dioxo-1H-1,4-benzodiazepin-3-carbonsäureester der allgemeinen Formel III sind bisher nicht bekannt.1,4-benzodiazepine-2,5-diones were prepared by reaction of isatoic anhydrides with glycine ester in pyridine (GM Coppola, Synthesis 1980, 055; DH Kim, J. Heterocycl.Chem., 12, 1323 (1975)) or with glycine in acetic acid (Gates, J. Org., Chem., 45, 1675 [198O]), but these methods do not result in compounds containing functional groups in the 3-position: 2,3,4,5-tetrahydro-2 , 5-dioxo-1H-1,4-benzodiazepine-3-carboxylic acid esters of general formula III are not yet known.
Ziel der ErfindungObject of the invention
Ziel der Erfindung ist es, biologisch aktive 2,5-Dioxo-1,4-benzodiazepin-3-carbonsäureester der Praxis als Wirkstoffe zur Verfugung zu stellen.The aim of the invention is to provide biologically active 2,5-dioxo-1,4-benzodiazepine-3-carboxylic acid esters of 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 vonThe object of the invention is a process for the preparation of
2,3,4,5-Tetrahydro-2,5-dioxo-1H-1,4-benzodiazepin-3-carbonsäureestern der allgemeinen Formel III zu entwickeln.To develop 2,3,4,5-tetrahydro-2,5-dioxo-1H-1,4-benzodiazepine-3-carboxylic acid esters of general formula III.
Erfindungsgemäß wird ein Isatosäureanhydrid der allgemeinen Formel I in Lösung oder Suspension in einem dipolar-aprotischen Lösungsmittel unter Erwärmen mit einem Aminomalonsäureester der allgemeinen Formel Il zur entsprechenden Verbindung der allgemeinen Formel III umgesetzt.According to the invention, an isatoic anhydride of the general formula I is reacted in solution or suspension in a dipolar aprotic solvent with heating with an aminomalonic acid ester of the general formula II to give the corresponding compound of the general formula III.
In den allgemeinen Formeln I bis III stehen R für Alkyl, Alkoxy, Halogen, CN, NO2 oder CF3, R1 für Alkyl (C1-C4) und η für 0 bis 4, wobei in den Fällen η = 2, 3 oder 4 die R gleich oder verschieden sind.In the general formulas I to III, R is alkyl, alkoxy, halogen, CN, NO 2 or CF 3 , R 1 is alkyl (C 1 -C 4 ) and η is 0 to 4, where in the cases η = 2, 3 or 4 the Rs are the same or different.
Werden die Salze der Verbindungen der allgemeinen Formel Il verwendet, so wird die Reaktion in Gegenwart einer Hilfsbase durchgeführt.If the salts of the compounds of the general formula II are used, the reaction is carried out in the presence of an auxiliary base.
Als Lösungsmittel eignen sich beispielsweise Dimethylformamid, Dimethylacetamid, Dimethylsulfoxid und Acetonitril.Suitable solvents are, for example, dimethylformamide, dimethylacetamide, dimethyl sulfoxide and acetonitrile.
Das erfindungsgemäße Verfahren ermöglicht erstmalig die Herstellung der Verbindungen der aligemeinen Formel III. Die Verbindungen der allgemeinen Formel III sind biologisch aktiv. Unter ihnen befinden sich solche, die eine fungizide und/oder pflanzenwachstumsregulatorische Wirkung zeigen.The process according to the invention makes it possible for the first time to prepare the compounds of general formula III. The compounds of general formula III are biologically active. Among them are those which have a fungicidal and / or plant growth regulatory effect.
Die Erfindung wird nachstehend durch Ausführungsbeispiele erläutert.The invention will be explained below by embodiments.
424 mg Aminomalonsäurediethylesterhydrochlorid, 642 mg 6,8-Dibrom-isatosäureanhydrid (I: (R)n = 6,8-Br2) und 0,274 ml Triethylamin werden in 30 ml absolutem DMF 4 Stunden bei 60-70°C gerührt. Das DMF wird im Vakuum abdestilliert, der Rückstand mit Wasser versetzt und mit Ammoniak neutralisiert. Es wird abgesaugt und aus Ethanol umkristallisiert. Schmp.: 194-198°C, Ausbeute: 400 mg (49% d. Th.) an 7,9-Dibrom-2,3,4,5-tetrahydro-2,5-dioxo-1 H-1,4-benzodiazepin-3-carbonsäureethylester (III: (R)n = 6,8-Br2; R1 = C2H6)424 mg of diethyl aminomalonate hydrochloride, 642 mg of 6,8-dibromo-isatoic anhydride (I: (R) n = 6,8-Br 2 ) and 0.274 ml of triethylamine are stirred in 30 ml of absolute DMF at 60-70 ° C. for 4 hours. The DMF is distilled off in vacuo, the residue is mixed with water and neutralized with ammonia. It is filtered off and recrystallized from ethanol. Mp: 194-198 ° C, yield: 400 mg (49% of theory) of 7,9-dibromo-2,3,4,5-tetrahydro-2,5-dioxo-1H-1,4 ethylbenzodiazepine-3-carboxylate (III: (R) n = 6,8-Br 2 ; R 1 = C 2 H 6 )
2494 72494 7
H2NH 2 N
einon
COOR1 COOR 1
COOR1 COOR 1
Υ- COORi Υ- COORi
23.MA!1936*350i4423.MA! * 1,936 350i44
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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DD29069286A DD249475A1 (en) | 1986-05-29 | 1986-05-29 | PROCESS FOR THE PREPARATION OF 2,3,4,5-TETRAHYDRO-2,5-DIOXO-1H-1,4-BENZODIAZEPINE-3-CARBOXYLIC ACID ESTERS |
Applications Claiming Priority (1)
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DD29069286A DD249475A1 (en) | 1986-05-29 | 1986-05-29 | PROCESS FOR THE PREPARATION OF 2,3,4,5-TETRAHYDRO-2,5-DIOXO-1H-1,4-BENZODIAZEPINE-3-CARBOXYLIC ACID ESTERS |
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DD249475A1 true DD249475A1 (en) | 1987-09-09 |
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DD29069286A DD249475A1 (en) | 1986-05-29 | 1986-05-29 | PROCESS FOR THE PREPARATION OF 2,3,4,5-TETRAHYDRO-2,5-DIOXO-1H-1,4-BENZODIAZEPINE-3-CARBOXYLIC ACID ESTERS |
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1986
- 1986-05-29 DD DD29069286A patent/DD249475A1/en not_active IP Right Cessation
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