CH304312A - Process for the preparation of a new quinoxaline. - Google Patents

Process for the preparation of a new quinoxaline.

Info

Publication number
CH304312A
CH304312A CH304312DA CH304312A CH 304312 A CH304312 A CH 304312A CH 304312D A CH304312D A CH 304312DA CH 304312 A CH304312 A CH 304312A
Authority
CH
Switzerland
Prior art keywords
sep
formula
preparation
quinoxaline
new quinoxaline
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ciba Geigy filed Critical Ciba Geigy
Publication of CH304312A publication Critical patent/CH304312A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren     zur    Herstellung eines neuen     Chinoxalins.            Gegenstand    des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines neuen       Chinoxalins,    welches dadurch gekennzeichnet  ist,     dass    man eine Verbindung der Formel  
EMI0001.0006     
    worin N und Y bei der Reaktion sich abspal  tende Reste bedeuten, mit einer die     Atomgrup-          pier#ung        =N-CH2-CH2-N-    aufweisenden  Verbindung umsetzt.  



  Das so erhaltene     5,6,7,8-Dipyrido-(5',6',          2",3")-l,2.3.4-tetrahydro-ehinoxalin    der For  niel  
EMI0001.0012     
    schmilzt bei 187 . Es besitzt     Anti-Virus-Wir-          kung    und soll als Heilmittel Verwendung fin  den. So zeigt es sieh besonders wirksam gegen  über dem     Infliaenza-Virus    im Hühnerembryo.

      Als Ausgangsstoffe verwendet man vor  teilhaft einerseits     4,7-Phenanthrolin-5,6-chi-          non        und    anderseits     Äthylendiamin-(1,2)    oder       Äthylenharnstoff.    Das     Äthylendiamin    kann  auch in Form seiner Salze verwendet werden.  Die Reaktion wird zweckmässig in Anwesen  heit eines     Verdünnungsmittels    durchgeführt.  Das als Ausgangsstoff     verwendete        4,7-Phen-          aiithrolin-5,6-ehinon    kann nach dem Verfah  ren des Schweiz. Patentes     Nr.293298    herge  stellt werden.  



       Beispiel:     20 Gewichtsteile     4,7-Phenanthrolin-5,6-chi-          non    werden in 1000     Volumteilen    Methanol ge  löst und mit 6 Gewichtsteilen     Äthylendiamin     versetzt. Die Reaktion tritt sofort. ein, sehr       wahrscheinlich    zunächst unter     Bildung    von       5,6,7,8-Dipyrido-        (5',6',2",3")        -dihy        dr        o-chinoxa-          lin    der Formel  
EMI0001.0040     
    Man dampft dann ein.

   Aus dem Rückstand  lassen sieh durch Umkristallisation aus Me-           thanol    die nachstehenden zwei Produkte iso  lieren. Das eine ist das     5,6,7,8-Dip7rido-(5',6'-          2",3")-eIiinoxalin    der Formel  
EMI0002.0004     
         welehes,    aus Methanol weiter     umkristallisiert,     einen F. von     270     zeigt. Das andere Produkt  stellt das 5,6,     7,8-Dipyrido-(5',6',2",3")-1,2,3.-1-          tetraliydro-ehinoxalin    der Formel  
EMI0002.0010     
    dar; es ist in Essigester und Benzol gut lös  lich und     schmilzt.    bei 187 .



  Process for the preparation of a new quinoxaline. The present patent relates to a process for the preparation of a new quinoxaline, which is characterized in that a compound of the formula
EMI0001.0006
    where N and Y are radicals which split off during the reaction, with a compound having the atomic group = N-CH2-CH2-N-.



  The 5,6,7,8-dipyrido (5 ', 6', 2 ", 3") -1, 2.3.4-tetrahydro-ehinoxaline of the formula obtained in this way
EMI0001.0012
    melts at 187. It has anti-virus effects and is said to be used as a remedy. It shows that it is particularly effective against the infliaenza virus in the chicken embryo.

      The starting materials used are on the one hand 4,7-phenanthroline-5,6-quinon and on the other hand ethylene diamine (1,2) or ethylene urea. The ethylenediamine can also be used in the form of its salts. The reaction is conveniently carried out in the presence of a diluent. The 4,7-phen-aiithroline-5,6-ehinone used as the starting material can be processed according to the Swiss method. Patent No. 293298 can be manufactured.



       Example: 20 parts by weight of 4,7-phenanthroline-5,6-quinon are dissolved in 1000 parts by volume of methanol and 6 parts by weight of ethylenediamine are added. The reaction occurs immediately. one, very likely initially with the formation of 5,6,7,8-dipyrido (5 ', 6', 2 ", 3") -dihydr o-quinoxaline of the formula
EMI0001.0040
    You then evaporate.

   The following two products can be isolated from the residue by recrystallization from methanol. One is the 5,6,7,8-dip7rido- (5 ', 6'- 2 ", 3") -elinoxaline of the formula
EMI0002.0004
         welehes, further recrystallized from methanol, shows an F. of 270. The other product is the 5,6,7,8-dipyrido (5 ', 6', 2 ", 3") - 1,2,3.-1-tetraliydro-ehinoxaline of the formula
EMI0002.0010
    dar; it is easily soluble in ethyl acetate and benzene and melts. at 187.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung, eines neuen Chinoxalins, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0002.0013 EMI0002.0014 worin <SEP> Z <SEP> und <SEP> Y <SEP> bei <SEP> der <SEP> Reaktion <SEP> sieh <SEP> abspal tende <SEP> Reste <SEP> bedeuten, <SEP> mit <SEP> einer <SEP> die <SEP> Atomgrup pierung <SEP> =N-CH.-CH.-N <SEP> - <SEP> aufweisenden <tb> Verbindung <SEP> umsetzt. <tb> Das <SEP> so <SEP> erhaltene <SEP> 5,6,7,8-Dipyi@ido-(5',6', <tb> '",3" <SEP> )-1,2, <SEP> 3,4-tetrahyclro-ehinoxalin <SEP> der <SEP> For mel EMI0002.0015 schmilzt bei 187 . PATENT CLAIM: Process for the production of a new quinoxaline, characterized in that a compound of the formula EMI0002.0013 EMI0002.0014 where <SEP> Z <SEP> and <SEP> Y <SEP> for <SEP> the <SEP> reaction <SEP> see <SEP> mean <SEP> split off <SEP> residues, <SEP> with <SEP> a <SEP> having the <SEP> atom group <SEP> = N-CH.-CH.-N <SEP> - <SEP> <tb> connection <SEP> implemented. <tb> The <SEP> so <SEP> received <SEP> 5,6,7,8-Dipyi @ ido- (5 ', 6', <tb> '", 3" <SEP>) -1,2, <SEP> 3,4-tetrahyclro-ehinoxaline <SEP> of the <SEP> formula EMI0002.0015 melts at 187. Es besitzt. Anti-Virus-Wir- kung und soll als Heilmittel Verwendung fin den, EMI0002.0019 <B>UNTERANSPRÜCHE:</B> EMI0002.0020 1. <SEP> Verfahren <SEP> nach <SEP> Patentansprueli, <SEP> da dureli <SEP> gekennzeiehnet, <SEP> dass <SEP> man <SEP> 4,7-Phen anthi,olin-5,6-ehinon <SEP> als <SEP> Ausgangsstoff <SEP> ver wendet. <tb> '. <SEP> Verfahren <SEP> nach <SEP> Patentanspruch <SEP> und <tb> I?nteraiisprneh <SEP> 1, <SEP> dadureh <SEP> gekennzeichnet, <tb> dass <SEP> man <SEP> mit <SEP> Äthylendianiiii-(7,2-? <SEP> umsetzt. It owns. Anti-virus effect and should be used as a remedy, EMI0002.0019 <B> SUBClaims: </B> EMI0002.0020 1. <SEP> method <SEP> according to <SEP> patent claims, <SEP> because dureli <SEP> marked, <SEP> that <SEP> man <SEP> 4,7-phen anthi, olin-5,6-ehinon <SEP> used as <SEP> starting material <SEP>. <tb> '. <SEP> method <SEP> according to <SEP> patent claim <SEP> and <tb> I? nteraiisprneh <SEP> 1, <SEP> dadureh <SEP> marked, <tb> that <SEP> you <SEP> with <SEP> Äthylendianiiii- (7,2-? <SEP>.
CH304312D 1950-05-05 1950-05-05 Process for the preparation of a new quinoxaline. CH304312A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH304312T 1950-05-05
CH301251T 1950-05-05

Publications (1)

Publication Number Publication Date
CH304312A true CH304312A (en) 1954-12-31

Family

ID=25734315

Family Applications (1)

Application Number Title Priority Date Filing Date
CH304312D CH304312A (en) 1950-05-05 1950-05-05 Process for the preparation of a new quinoxaline.

Country Status (1)

Country Link
CH (1) CH304312A (en)

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