DE2742542A1 - Verfahren zur herstellung von 2-n, n-disubstituierten aminopyridinen - Google Patents

Verfahren zur herstellung von 2-n, n-disubstituierten aminopyridinen

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Publication number
DE2742542A1
DE2742542A1 DE19772742542 DE2742542A DE2742542A1 DE 2742542 A1 DE2742542 A1 DE 2742542A1 DE 19772742542 DE19772742542 DE 19772742542 DE 2742542 A DE2742542 A DE 2742542A DE 2742542 A1 DE2742542 A1 DE 2742542A1
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Prior art keywords
disubstituted
cobaltocene
acetylene
mol
reaction
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DE19772742542
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English (en)
Inventor
Peter Dipl Chem Dr Hardt
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Lonza AG
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Lonza AG
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Priority claimed from CH1213975A external-priority patent/CH612939A5/xx
Priority claimed from CH1307976A external-priority patent/CH622008A5/de
Priority claimed from CH947177A external-priority patent/CH630357A5/de
Application filed by Lonza AG filed Critical Lonza AG
Publication of DE2742542A1 publication Critical patent/DE2742542A1/de
Withdrawn legal-status Critical Current

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    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/08—Preparation by ring-closure
    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/22—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/57—Nitriles
    • 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)

Description

  • Verfahren zur Herstellung von 2-N,N-disubstituierten
  • Aminopyridinen.
  • Das Hauptpatent No. (Anmeldung P 26 15 309.3) betrifft ein Verfahren zur katalytischen Herstellung von 2-substituierten Pyridinen aus einer entsprechenden Cyanoverbindung und Acetylen und ist dadurch gekennzeichnet, dass die Umsetzung bei erhöhter Temperatur in Gegenwart von Kobaltocen als Katalysator durchgeführt wird.
  • Vorliegendes Zusatzpatent betrifft ein Verfahren zur Herstellung von 2-N,N-disubstituierten Aminopyridinen der allgemeinen Formel worin R1 und R2 gleich oder verschieden sein können und eine Alkyl-, Cycloalkyl- oder Arylgruppe beaeuten oder eine Piperidino-, Pyrrolidino- oder Morpholinogruppe darstellen.
  • Das Verfahren ist dadurch gekennzeichnet, dass man N,N-disubstituierte Cyanamide der allgemeinen Formel worin R1 und R2 oder die genannte Bedeutung hulwen, mit Acetylen in Gegenwart von Kobaltocen als Katalysator bei erhöhtem Druck und Temperatur umsetzt.
  • Als Kobaltocen wird die Verbindung Bis-cyclopentadienylkobalt bezeichnet. Dieser Katalysator ist einfach zu handhaben und kann leicht aus einfachen Edukten hergestellt werden. Ein besonderer Vorteil bei der Verwendung von Kobaltocen als Katalysator besteht darin, dass dieser Katalysator bei hohen Temperaturen oberhalb von 800C verwendet werden kann. Damit werden raschere und vollständigere Umsätze der Cyanoverbindung erreicht, ohnc die bekannten Nebenreaktionen des acceylens mit sich selbst zu Benzol und Polymeren zu beqünstigen.
  • Als N,N-disubstituierte Cyanamide kommen vorzugsweise solche in Frage, in denen die Reste R1 und R2, sofern sie Alkylreste bedeuten, je bis zu t3 C-Atome, insbesondere bis zu 6 C-Atome aufweisen. Sie können geradkettig oder verzweigt sein.
  • Cycloalkylreste für R1 und R, sind vorzugsweise solche mit 5 - 8 C-Atomen, während für diese Reste stehende Arylgruppen, vorzugsweise Phenyl- oder Naphthylgruppen sind.
  • Bevorzugt kommen N,N-I)imethylcyanamid, N,N-Dicyclohexylcyanamid, N-Methyl-, N-(ß-cyanoäthyl)-cyanamid, N-Methyl-, N-Phenylcyanamid, N-Methyl-, N-Cyclohexyl-cyanamid, N-Cyanopiperidin, N-Cyanopyrolidin oder N-Cyanomorpholin zur Anwendung.
  • Die N,N-Dialkylcyanamide ihrerseits können leich auf bekannte Weise aus Chlorcyan und entsprechenden sekundären Aminen hergestellt werden, beschrieben beispielsweise in d'r belgischen Patentschrift 641 601.
  • Zur Ausführung des erfindungsgemässen Verfahrens werden die entsprechenden Cyanantidverbindungen und Kobaltocen in einem Druckgefäss mit Acetylen gesättigt und erwärmt.
  • Vorzugsweise wird die Umsetzung bei 10 bis 25 bar und Temperaturen von 70 bis 1800C ausgeführt.
  • Die vorzugsweise angewendete Menge an Kobaltocen beträgt 0,5 bis 2,0 Gew.%. bezogen auf das eingesetzte Cyanamid.
  • Umgesetztes Acetylen wird chargenweise nachgepresst oder laufend nachgespiesen.
  • Durch die Wahl von Katalysatormenge, Druck und Temperatur in den angegebenen Grenzen lassen sich mehr als 20 Mol Cyanoverbindung pro Mol Katalysator und Stunde umsetzen.
  • Zweckunjssigerweise werden die Peaktionsansätze durch Destillation aufgearbeitet. Ein hierbei anfallender Vorlauf aus nicht umgesetzter Cyanoverbindung, gegebenenfalls auch ein Gemisch mit Benzol, kann bei weiteren Ansätzen wieder verwendet werden.
  • Für die Durchführung der Reaktion ist normalerweise kein Lösungsmittel erforderlich, jedoch können zur besseren Wärmeabfuhr bei der exothermen Reaktion inerte Lösungsmittel, beispielsweise Benzol oder die herzustcllende Pyridinverbindung, als Verdünnungsmittel verwendet werden.
  • Das Verfahren kann auch kontinuierlich durchgeführt werden, beispielsweise in einem Strömungsrohr.
  • Beispiel 1 Unter Stickstoff werden 3,1 g Kobaltocen (0,016 Mol) in 44,0 g Benzol gelöst, mit 164 g wasserfreiem N,N-Dimethylcyanamid (2,3 Mol) versetzt und in einem 1 Liter-Rührautoklaven bei 200C mit 12 atm Acetylen gesättigt. Man erwärmt auf 700C, wartet den Beginn der exothermen Reation ab und steigert'die Heizung vorsichtig so, dass im Autoklaven eine Temperatur von 1600C herrscht. Nach dem Druckabfall im Autoklaven auf unter 12 atm wird Acetylen nachgepresst. Nach 10 Stunden Reaktionszeit wird abgekühlt und.entspannt. Durch fraktionierende Destillation wurden nach Benzol und geringen Mengen N,N-Dimethylcyanamid 238 g 2-(N,N-Dimethylamino)-pyridin (Kp 920C/21 Torr) in einer Reinheit von 99,8t erhalten, entsprechend einer Ausbeute von 84,5%.
  • Beispiel 2 Analog Beispiel 1 wurden 1,0 g Kobaltocen (0,005 Mol), 44,0 g Benzol und 99,1 g wasserfreies N-Cyanopiperidin (0,9 Mol) im Autoklaven 10 Stunden bei 70 bis 1700C mit Acetylen behandelt. Durch Destillation des Reaktionspvoduktes wurden neben Benzol 10,3 g N-Cyanopiperidin und 116,2 g 2-(N-Piperidino)-pyridir) erhalten, entsprechend einer Ausbeute von 79,6%.
  • Beispiel 3 Analog Beispiel 1 wurden 2,0 g Kobaltocen (0,011 Mol), 180 g 2-(N,N-Dimethylamino)-pyridin und 57,5 g wasserfreies N,N-Dimethylcyanamid (0,8 Mol) 6 Stunden bei 125 bis 170°C mit Acetylen behandelt. Man erhält 284 9 eines Rohproduktes, aus welchem durch fraktionierende Destillation nach einem kleiner Vorlauf aus Benzol und N,N-Dimethylcyanamid 268,7 g 2-(N,N-Dimethylamino)-pyridin erhalten wurden. Das entspricht einer Ausbeute von 88,5% bzw. 84,8% auf umgesetztes Acetylen.
  • Beispiel 4 Analog Beispiel 1 wurden 1,1 g Kobaltocen (0,006 Mol) und 75,0 g N-Mcthyl-, N-Phenyl-cyanamid (0,57 Mol) iflI Autoklaven 12 Stunden bei 120 bis 1700C mit Acetylen behandelt. Aus dem Reaktionsgut wurden durch Destillation 55,2 g Eduktendung und 15,5 g 2-(N-Methyl, N-Phenylamino)-pyridin erhalten. Das entspricht einer Ausbeute von 56 %, bezogen auf umgesetzte Cyanoverbindung.
  • Beispiel 5 Gemäss Beispiel 1 wui:dcn aus 0,6 cj Vobaltocen (0,003 Mol), 70 ml Benzol und 49,2 g N-Cyanopyrrolidin (0,5 Mol) nach 8 Stunden Reaktion mit: Acetylen im Autoklaven bei 130 bis 170°C und Destillation 46,4 g 2-(N-Pyrrolidino)-pyridin erhalten (61% Ausbeute).
  • Beispiel 6 Gemäss Beispiel 1 wurden aus 1,0 9 Kobaltocen (0,005 Mol), 150 ml Benzol und 100 g N-Cyanomorpholin (0,89 Mol) nach einer Reaktionszeit von 7 Stunden bei 80 bis 1600C und Destillation 114,3 g 2-(N-Morpholino)-pyridin erhalten (78% Ausbeute).

Claims (3)

  1. Patentansprüche: 10 Verfahren zur Herstellung von 2-N,N-disubstituierten kninopyridinen der allgemeinen Formel worin R1 und R2 gleich oder verschieden sein können und eine Alkyl-, Cycloalkyl- oder Arylgruppe bedeuten oder eine Piperidino-, Pyrrolidino- oder Morpholinogruppe darstellen, dadurch gckellnzeichnet, dass man N,N-disubstituierte Cyanamide der allgemeinen Formel worin R1 und R2 oder die genannte Bedeutung haben, mit Acetylen in Gegenwart von Kobaltocen als Katalysator bei erhöhtem Druck und Temperatur umsetzt.
  2. 2. Verfahren gemäss Patentanspruchl,dadurch gekennzeichnct, dass man die Umsetzung bei Drücken von 10 bis 25 bar und Temperaturen von 70 bis 1800C ausführt.
  3. 3. Verfahren gemäss Patentanspruch 1 - 2, dadurch gekennzeichnet, dass man die Umsetzung in Gegenwart von 0,5 bis 2,0 Gew.% Kobaltocen, bezogen auf eingesetztes Cyanamid, ausführt.
DE19772742542 1975-09-18 1977-09-21 Verfahren zur herstellung von 2-n, n-disubstituierten aminopyridinen Withdrawn DE2742542A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH1213975A CH612939A5 (de) 1975-09-18 1975-09-18
CH1307976A CH622008A5 (en) 1976-10-15 1976-10-15 Process for the catalytic preparation of beta-substituted 2-ethylpyridines
CH947177A CH630357A5 (en) 1977-08-02 1977-08-02 Process for the preparation of 2-N,N-disubstituted aminopyridines

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DE2742542A1 true DE2742542A1 (de) 1979-02-15

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DE19762615309 Granted DE2615309A1 (de) 1975-09-18 1976-04-08 Verfahren zur katalytischen herstellung von 2-substituierten pyridinen
DE19772742542 Withdrawn DE2742542A1 (de) 1975-09-18 1977-09-21 Verfahren zur herstellung von 2-n, n-disubstituierten aminopyridinen

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DE19762615309 Granted DE2615309A1 (de) 1975-09-18 1976-04-08 Verfahren zur katalytischen herstellung von 2-substituierten pyridinen

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Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH601234A5 (de) * 1976-11-15 1978-06-30 Lonza Ag
DE2840460C2 (de) * 1978-09-16 1980-12-11 Studiengesellschaft Kohle Mbh, 4330 Muelheim Katalytisches Verfahren zur Herstellung von 2-Vinylpyridin aus Acetylen und Acrylnitril
DE3117363A1 (de) * 1981-05-02 1982-11-18 Studiengesellschaft Kohle mbH, 4330 Mülheim Verfahren zur herstellung von pyridin und pyridinderivaten aus alkinen und cyanoverbindungen in gegenwart von cobalt- bzw. rhodium-komplexverbindungen mit borhaltigen liganden
US4477673A (en) * 1982-01-27 1984-10-16 Ciba-Geigy Corporation Process for the preparation of substituted divinylpyridines and novel substituted divinylpyridines
WO1999065897A1 (en) 1998-06-19 1999-12-23 Chiron Corporation Inhibitors of glycogen synthase kinase 3

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE846350A (fr) * 1975-09-18 1977-03-17 Procede de preparation catalytique de pyridines substituees en position 2

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3829429A (en) * 1970-01-07 1974-08-13 Du Pont Catalytic synthesis of substituted pyridines from acetylenes and nitriles
DE2416295C3 (de) * 1974-04-04 1980-01-10 Studiengesellschaft Kohle Mbh, 4330 Muelheim Verfahren zur Herstellung von ein- oder mehrfach substituierten Pyridinen durch katalytische Mischcyclisierung von Alkinen mit Nitrilen in Gegenwart einer Kobalt-Komplexverbindung

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE846350A (fr) * 1975-09-18 1977-03-17 Procede de preparation catalytique de pyridines substituees en position 2

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DE2615309A1 (de) 1977-03-24
DE2615309C2 (de) 1987-02-12

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