DD263062A1 - PROCESS FOR SYNTHESIS OF SUBSTITUTED 2,3-DIHYDRO-5H-1,2,4-TRIAZOLO [3,4-B] CHINAZOLIN-3-ONES AND 1,2,3,4-TETRAHYDRO-5H, 7H-1,2 , 4-TRIAZEPINO [3.4-B] -CHIAZOLIN-5-ones - Google Patents
PROCESS FOR SYNTHESIS OF SUBSTITUTED 2,3-DIHYDRO-5H-1,2,4-TRIAZOLO [3,4-B] CHINAZOLIN-3-ONES AND 1,2,3,4-TETRAHYDRO-5H, 7H-1,2 , 4-TRIAZEPINO [3.4-B] -CHIAZOLIN-5-ones Download PDFInfo
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Abstract
Die Erfindung betrifft ein neues Verfahren zur Herstellung der bisher nicht bekannten substituierten 2,3-Dihydro-5H-1,2,4-triazolo&3,4-b!chinazolin-3-one und 1,2,3,4-Tetrahydro-5H,7H-1,2,4-triazepino&3,4-b!chinazolin-5-one in Form ihrer Hydrochloride der allgemeinen Formel 2 und 3, die als Zwischenprodukte fuer die Zubereitung biologisch aktiver Praeparate anwendbar sind. Die Synthese erfolgt durch Umsetzung substituierter 2-Hydrazino-3,4-dihydrochinazoline der allgemeinen Formel 1 mit Chlorameisensaeureethylester bzw. 3-Halogen-alkansaeuren in einem unpolaren Loesungsmittel.The invention relates to a novel process for preparing the hitherto unknown substituted 2,3-dihydro-5H-1,2,4-triazolo & 3,4-b! Quinazolin-3-ones and 1,2,3,4-tetrahydro-5H , 7H-1,2,4-triazepino & 3,4-b! Quinazolin-5-ones in the form of their hydrochlorides of general formula 2 and 3, which are useful as intermediates for the preparation of biologically active preparations. The synthesis is carried out by reacting substituted 2-hydrazino-3,4-dihydroquinazolines of the general formula 1 with ethyl chloroformate or 3-haloalkanoic acids in a non-polar solvent.
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Die Erfindung betrifft ein Verfahren zur Herstellung von substituierten 2,3-Dihydro-5H-1,2,4-triazolo[3,4-b]chinazolin-3-onen und i^^^-Tetrahydro-SH^H-i^^-triazepinofSAblchinazolin-B-onen in Form ihrer Hydrochloride der allgemeinen Formel 2 und 3, die man in hoher Reinheit und guten Ausbeuten durch Reaktion von 3-Halogen-alkansäuren bzw. Chlorameisensäureester mit 2-Hydrazino-3,4-dihydrochinazolinen erhält. Diese Verbindungen sind als organisch chemische Zwischenprodukte für die Zubereitung potentiell biologisch aktiver Präparate einsetzbar.The invention relates to a process for the preparation of substituted 2,3-dihydro-5H-1,2,4-triazolo [3,4-b] quinazolin-3-ones and i ^^^ - tetrahydro-SH ^ Hi ^^ - triazepinofSAblchinazolin-B-ons in the form of their hydrochlorides of the general formula 2 and 3, which is obtained in high purity and good yields by reaction of 3-haloalkanoic acids or chloroformate with 2-hydrazino-3,4-dihydroquinazolines. These compounds can be used as organic chemical intermediates for the preparation of potentially biologically active preparations.
Die erfindungsgemäß beschriebenen substituierten 2,3-Dihydro-5H-1,2,4-triazolo[3,4-b]chinazolin-3-one und 1,2,3,4-Tetrahydro-5H,7H-1,2,4-triazepino[3,4-blchinazolin-5-one in Form ihrer Hydrochloride entsprechend der allgemeinen Formel 2 und 3 sind noch nicht bekannt, es existiert somit noch kein Verfahren zu ihrer Herstellung.The substituted 2,3-dihydro-5H-1,2,4-triazolo [3,4-b] quinazolin-3-ones and 1,2,3,4-tetrahydro-5H, 7H-1,2 described in the invention, 4-triazepino [3,4-blinazolin-5-ones in the form of their hydrochlorides corresponding to the general formula 2 and 3 are not yet known, thus there is no process for their preparation.
Ziel der Erfindung ist es, ein einfaches Verfahren zur Synthese potentiell biologisch-aktiver substituierter 2,3-Dihydro-5H-1,2,4-triazolo[3,4-b]chinazolin-3-one und 1,2,3,4-Tetrahydro-5H,7H-1,2,4-triazepino[3,4-b]chinazolin-5-one bzw. deren Hydrochloride zu finden, da.derartige Verbindungen bisher nicht zugänglich sind.The aim of the invention is to provide a simple method for the synthesis of potentially biologically active substituted 2,3-dihydro-5H-1,2,4-triazolo [3,4-b] quinazolin-3-ones and 1,2,3, 4-tetrahydro-5H, 7H-1,2,4-triazepino [3,4-b] quinazolin-5-ones or their hydrochlorides find da.derartige compounds are not yet accessible.
a) Lösung der technischen Aufgabea) Solution of the technical problem
Erfindungsgemäß wird die Aufgabe dadurch gelöst, daß ein einfaches, billiges und leicht durchführbares Verfahren zur Herstellung bisher nichtzugänglicher substituierter2,3-Dihydro-5H-1,2,4-triazolo[3,4-b]chinazolin-3-one und 1,2,3,4-Tetrahydro-5H,7H-1,2,4-triazepino[3,4-b]chinazolin-5-one gefunden wurde und ein nützlicher Effekt durch die Verwendung von handelsüblichem Toluen als Lösungsmittel und 3-Chlor-propionsäure bzw. Chlorameisensäureester als gängige Ausgangsstoffe eintritt.According to the invention the object is achieved by a simple, inexpensive and easy to carry out process for preparing previously inaccessible substituted 2,3-dihydro-5H-1,2,4-triazolo [3,4-b] quinazolin-3-ones and 1, 2,3,4-tetrahydro-5H, 7H-1,2,4-triazepino [3,4-b] quinazolin-5-one was found and a useful effect by the use of commercial toluene as a solvent and 3-chloro Propionic acid or chloroformate as common starting materials occurs.
b) Merkmale der Erfindungb) Features of the invention
Entsprechend der Erfindung erfolgt die Lösung der Aufgabe dadurch, daß alkyl-, aryl- oder halogensubstituierte 2-Hydrazino-3,4-dihydrochinazoline der allgemeinen Formel 1 mit Chlorameisensäureethylester bzw. 3-Halogen-alkansäuren, bevorzugt 3-Chlorpropionsäurezu den entsprechend substituierten 2,3-Dihydro-5H-1,2,4-triazolo[3,4-b]chinazolin-3-onen und 1,2,3,4-Tetrahydro-5H,7H-1,2,4-triazepino[3,4-b]chinazolin-5-onen, die man als Hydrochloride erhält und der allgemeinen Formel 2 und 3 entsprechen, in einem inerten Lösungsmittel wie Toluen umgesetzt werden.According to the invention, the object is achieved in that alkyl, aryl or halogen-substituted 2-hydrazino-3,4-dihydroquinazolines of the general formula 1 with ethyl chloroformate or 3-haloalkanoic acids, preferably 3-chloropropionic acid to the appropriately substituted 2, 3-Dihydro-5H-1,2,4-triazolo [3,4-b] quinazolin-3-ones and 1,2,3,4-tetrahydro-5H, 7H-1,2,4-triazepino [3, 4-b] quinazolin-5-ones, which are obtained as hydrochlorides and correspond to the general formula 2 and 3, are reacted in an inert solvent such as toluene.
5-Phenyl-2,3-dihydro-5H-1,2,4-triazolo[3,4-b]chinazolin-3-on-hydrochlorid(2a) 0,24g (0,001 mol) 2-Hydrazino-4-phenyl-3,4-dihydrochinazolin (1a) werden in 25 ml wasserfreiem Toluen gelöst und mit 0,11g (0,001 mol) Chlorameisensäureethylester versetzt. Man erhitzt 6 Stunden unter Rückfluß und entfernt anschließend das Lösungsmittel im Vakuum. Das zurückbleibende Öl wird mit wenig Ethanol oder i-Propanol durch kurzes Erwärmen aufgenommen und nach dem Abkühlen saugt man die ausgefallenen Kristalle ab. Zur Vervollständigung der Fällung kann mit etwas Wasser verdünnt werden.5-phenyl-2,3-dihydro-5H-1,2,4-triazolo [3,4-b] quinazolin-3-one hydrochloride (2a) 0.24 g (0.001 mol) of 2-hydrazino-4-phenyl -3,4-dihydroquinazoline (1a) are dissolved in 25 ml of anhydrous toluene and treated with 0.11 g (0.001 mol) of ethyl chloroformate. The mixture is heated under reflux for 6 hours and then the solvent is removed in vacuo. The residual oil is taken up with a little ethanol or i-propanol by brief heating and after cooling, the precipitated crystals are filtered off with suction. To complete the precipitation can be diluted with a little water.
Ausbeute: 79% der Theorie Schmelzpunkt: 350-353cC (Ethanol) Die freie Base läßt sich auf die übliche Art durch Alkalisieren mit NaHCO3-Lösung gewinnen.Yield: 79% of theory Melting point: 350-353 c C (ethanol) The free base can be obtained in the usual way by alkalization with NaHCO 3 solution.
7-Chlor-5-phenyl-2,3-dihydro-5H-1,2,4-triazolo[3,4-b]chinazolin-3-on-hydrochlorid(2b) Analog Beispiel 1 aus e-Chlor^-hydrazino^-phenyl-SAdihydro-chinazolin (1 b) und Chlorameisensäureethylester Ausbeute: 82% der Theorie Schmelzpunkt: 345-348°C7-Chloro-5-phenyl-2,3-dihydro-5H-1,2,4-triazolo [3,4-b] quinazolin-3-one hydrochloride (2b) Analogously to Example 1 from e-chloro-hydrazino ^ -phenyl-S-dihydro-quinazoline (1 b) and ethyl chloroformate Yield: 82% of theory Melting point: 345-348 ° C
7-Phenyl-1,2,3,4-tetrahydro-5H,7H-1,2,4-triazepino[3,4-b]chinazolin-5-on-hydrochlorid(3a) Analog Beispiel 1 aus 2-Hydrazino-4-phenyl-3,4-dihydro-chinazolin (1 a) und 3-Chlor-propionsäure Ausbeute: 51 % der Theorie Schmelzpunkt: 197-199°C (Ethanol)7-phenyl-1,2,3,4-tetrahydro-5H, 7H-1,2,4-triazepino [3,4-b] quinazolin-5-one hydrochloride (3a) Analogously to Example 1 from 2-hydrazino 4-phenyl-3,4-dihydro-quinazoline (1 a) and 3-chloropropionic acid Yield: 51% of theory Melting point: 197-199 ° C (ethanol)
9-Chlor-7-phenyl-1,2,3,4-tetrahydro-5H,7H-1 ^A-triazepinoß/l-blchinazolin-S-on-hydrochlorid (3 b) Analog Beispiel 1 aus 6-Chlor-2-hydrazino-4-phenyl-3,4-dihydrochinazolin (1 b) und 3-Chlor-propionsäure Ausbeute: 58% der Theorie Schmelzpunkt: 199-2030C9-Chloro-7-phenyl-1,2,3,4-tetrahydro-5H, 7H-1 ^ A-triazepino-β / 1-iminazolin-S-on-hydrochloride (3b) Analogous to Example 1 from 6-chloro-2 hydrazino-4-phenyl-3,4-dihydroquinazolin (1 b) and 3-chloro-propionic acid yield: 58% of theory melting point: 199-203 0 C.
Claims (6)
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DD30535987A DD263062A1 (en) | 1987-07-27 | 1987-07-27 | PROCESS FOR SYNTHESIS OF SUBSTITUTED 2,3-DIHYDRO-5H-1,2,4-TRIAZOLO [3,4-B] CHINAZOLIN-3-ONES AND 1,2,3,4-TETRAHYDRO-5H, 7H-1,2 , 4-TRIAZEPINO [3.4-B] -CHIAZOLIN-5-ones |
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DD30535987A DD263062A1 (en) | 1987-07-27 | 1987-07-27 | PROCESS FOR SYNTHESIS OF SUBSTITUTED 2,3-DIHYDRO-5H-1,2,4-TRIAZOLO [3,4-B] CHINAZOLIN-3-ONES AND 1,2,3,4-TETRAHYDRO-5H, 7H-1,2 , 4-TRIAZEPINO [3.4-B] -CHIAZOLIN-5-ones |
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DD30535987A DD263062A1 (en) | 1987-07-27 | 1987-07-27 | PROCESS FOR SYNTHESIS OF SUBSTITUTED 2,3-DIHYDRO-5H-1,2,4-TRIAZOLO [3,4-B] CHINAZOLIN-3-ONES AND 1,2,3,4-TETRAHYDRO-5H, 7H-1,2 , 4-TRIAZEPINO [3.4-B] -CHIAZOLIN-5-ones |
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CN110872307A (en) * | 2019-06-05 | 2020-03-10 | 河南科技大学第一附属医院 | Thiazole medicine molecule used in hospital and gynecology and preparation method and application thereof |
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CN110872307A (en) * | 2019-06-05 | 2020-03-10 | 河南科技大学第一附属医院 | Thiazole medicine molecule used in hospital and gynecology and preparation method and application thereof |
CN110872307B (en) * | 2019-06-05 | 2020-07-10 | 河南科技大学第一附属医院 | Thiazole medicine molecule used in hospital and gynecology and preparation method and application thereof |
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