WO2000059883A3 - Verfahren zur herstellung von n-aryl-aza-heterocyclen in gegenwart von cesiumcarbonat - Google Patents

Verfahren zur herstellung von n-aryl-aza-heterocyclen in gegenwart von cesiumcarbonat Download PDF

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Publication number
WO2000059883A3
WO2000059883A3 PCT/EP2000/001574 EP0001574W WO0059883A3 WO 2000059883 A3 WO2000059883 A3 WO 2000059883A3 EP 0001574 W EP0001574 W EP 0001574W WO 0059883 A3 WO0059883 A3 WO 0059883A3
Authority
WO
WIPO (PCT)
Prior art keywords
aza
group
heterocycles
aryl
atoms
Prior art date
Application number
PCT/EP2000/001574
Other languages
English (en)
French (fr)
Other versions
WO2000059883A2 (de
Inventor
Hubert Barth
Klaus Steiner
Hans-Juergen Betche
Simon Schneider
Ulrich Bayer
Manfred Westermayer
Ulrike Wolfsperger
Original Assignee
Goedecke Gmbh
Hubert Barth
Klaus Steiner
Betche Hans Juergen
Simon Schneider
Ulrich Bayer
Manfred Westermayer
Ulrike Wolfsperger
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 Goedecke Gmbh, Hubert Barth, Klaus Steiner, Betche Hans Juergen, Simon Schneider, Ulrich Bayer, Manfred Westermayer, Ulrike Wolfsperger filed Critical Goedecke Gmbh
Priority to CA002360923A priority Critical patent/CA2360923A1/en
Priority to JP2000609395A priority patent/JP2002541143A/ja
Priority to BR0009432-3A priority patent/BR0009432A/pt
Priority to EP00916872A priority patent/EP1165512A2/de
Priority to AU38068/00A priority patent/AU3806800A/en
Priority to MXPA01009596A priority patent/MXPA01009596A/es
Priority to US09/889,341 priority patent/US6774242B1/en
Publication of WO2000059883A2 publication Critical patent/WO2000059883A2/de
Publication of WO2000059883A3 publication Critical patent/WO2000059883A3/de
Priority to US10/892,422 priority patent/US6933390B2/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrrole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Die Erfindung betrifft ein Verfahren zur Herstellung von N-Aryl-Aza-Heterocyclen der allgemeinen Formel (I) in der R1, R2, R3, R4 und R5 gleich oder verschieden sind und ein Wasserstoffatom, eine Nitrogruppe, eine Cyanogruppe, eine Alkoxycarbonylgruppe mit bis zu 5 C Atomen, eine Aldehydgruppe, eine Alkylcarbonylgruppe mit bis zu 5 C-Atomen, eine Arylcarbonylgruppe oder eine Amidgruppe bedeuten, wobei die Reste R1 bis R5 nicht alle gleichzeitig ein Wasserstoffatom sein können, und HETN einen aromatischen Aza-Heterocyclus mit insgesamt 5 oder 6 Ringatomen bedeutet, wobei bis zu 3 Ringatome Stickstoffatome sein können, und bis zu zwei weitere aromatische Kohlenstoffringe am Heterocyclus ankondensiert sein können, durch Reaktion von Aza-Heterocyclen mit aktivierten Aromaten der allgemeinen Formel (XIV) in der HAL für ein Halogenatom steht, unter Verwendung von Cesiumcarbonat ohne Zusatz von weiteren Katalysatoren bei Raumtemperatur.
PCT/EP2000/001574 1999-03-30 2000-02-25 Verfahren zur herstellung von n-aryl-aza-heterocyclen in gegenwart von cesiumcarbonat WO2000059883A2 (de)

Priority Applications (8)

Application Number Priority Date Filing Date Title
CA002360923A CA2360923A1 (en) 1999-03-30 2000-02-25 Process for the arylation of aza-heterocycles with activated aromatics in presence of caesium carbonate
JP2000609395A JP2002541143A (ja) 1999-03-30 2000-02-25 炭酸セシウムの存在下における活性芳香族化合物によるアザ複素環化合物のアリール化方法
BR0009432-3A BR0009432A (pt) 1999-03-30 2000-02-25 Processo para arilação de aza-heterociclos com aromáticos ativados na presença de carbonato de césio
EP00916872A EP1165512A2 (de) 1999-03-30 2000-02-25 Verfahren zur herstellung von n-aryl-aza-heterocyclen in gegenwart von cesiumcarbonat
AU38068/00A AU3806800A (en) 1999-03-30 2000-02-25 Method for arylating aza-heterocycles with activated aromatic compounds in the presence of cesium carbonate
MXPA01009596A MXPA01009596A (es) 1999-03-30 2000-02-25 Procedimiento para arilar aza-heterociclos con aromaticos activados en la presencia de carbonato de cesio.
US09/889,341 US6774242B1 (en) 1999-03-30 2000-02-25 Method for arylating aza-heterocycles with activated aromatic compounds in the presence of caesium carbonate
US10/892,422 US6933390B2 (en) 1999-03-30 2004-07-15 Process for the arylation of aza-heterocycles with activated aromatics in presence of caesium carbonate

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19914610.1 1999-03-30
DE19914610 1999-03-30

Related Child Applications (3)

Application Number Title Priority Date Filing Date
US09/889,341 A-371-Of-International US6774242B1 (en) 1999-03-30 2000-02-25 Method for arylating aza-heterocycles with activated aromatic compounds in the presence of caesium carbonate
US09889341 A-371-Of-International 2000-02-25
US10/892,422 Division US6933390B2 (en) 1999-03-30 2004-07-15 Process for the arylation of aza-heterocycles with activated aromatics in presence of caesium carbonate

Publications (2)

Publication Number Publication Date
WO2000059883A2 WO2000059883A2 (de) 2000-10-12
WO2000059883A3 true WO2000059883A3 (de) 2001-09-13

Family

ID=7903080

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/001574 WO2000059883A2 (de) 1999-03-30 2000-02-25 Verfahren zur herstellung von n-aryl-aza-heterocyclen in gegenwart von cesiumcarbonat

Country Status (8)

Country Link
US (2) US6774242B1 (de)
EP (1) EP1165512A2 (de)
JP (1) JP2002541143A (de)
AU (1) AU3806800A (de)
BR (1) BR0009432A (de)
CA (1) CA2360923A1 (de)
MX (1) MXPA01009596A (de)
WO (1) WO2000059883A2 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8029454B2 (en) 2003-11-05 2011-10-04 Baxter International Inc. High convection home hemodialysis/hemofiltration and sorbent system
DE102004010999A1 (de) 2004-03-06 2005-09-22 Wella Ag Kationische Naphthyldiazofarbstoffe sowie diese Farbstoffe enthaltende Mittel zur Färbung von Keratinfasern
EP1751121A2 (de) * 2005-04-06 2007-02-14 Sicor Inc. Verfahren zur herstellung von anastrozol
CN104788355A (zh) * 2015-04-02 2015-07-22 聊城大学 一种含氮杂环苯腈或邻苯二腈化合物的合成方法
WO2018165466A1 (en) * 2017-03-10 2018-09-13 Regents Of The University Of Minnesota Indole and indazole compounds and therapeutic uses thereof
CN106866561B (zh) * 2017-04-11 2019-04-23 中国工程物理研究院化工材料研究所 硝基或二硝基苯基-苯并[1,2,3]三唑、衍生物及制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5977361A (en) * 1997-10-16 1999-11-02 Yale University Transition metal-catalyzed process for preparing N-aryl compounds

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
DINSMORE C.J. & ZARTMAN C.B.: "Arylmethanesulfonates are convenient latent phenols in the nucleophilic aromatic substitution reaction", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 40, no. 21, 21 May 1999 (1999-05-21), pages 3989 - 3990, XP004164592, ISSN: 0040-4039 *
FLESSNER T. & DOYE S.: "Cesium carbonate: A powerful inorganic base in organic synthesis", JOURNAL FÜR PRAKTISCHE CHEMIE, CHEMIKER ZEITUNG, WILEY-VCH, WEINHEIM, DE, vol. 341, no. 2, February 1999 (1999-02-01), pages 186 - 190, XP002153415 *
GALE D.J. & WILSHIRE J.F.K.: "The preparation of sole polymethine Astrazon dyes", AUSTRALIAN JOURNAL OF CHEMISTRY, vol. 23, 1970, pages 1063 - 1068, XP000909779, ISSN: 0004-9425 *
LEE J.C. ET AL.: "Facile synthesis of alkyl phenyl ethers using cesium carbonate", SYNTHETIC COMMUNICATIONS, MARCEL DEKKER, INC., BASEL, CH, vol. 25, no. 9, September 1995 (1995-09-01), pages 1367 - 1370, XP000943391 *
MAIORANA S. ET AL.: "Aromatic nucleophilic substitution on haloarene chromium tricarbonyl complexes: Mild N-arylation of indoles", SYNTHESIS, GEORG THIEME VERLAG. STUTTGART, DE, May 1998 (1998-05-01), pages 735 - 738, XP002157809 *
MANN G. ET AL.: "Palladium-catalyzed C-N(sp2) bond formation: N-arylation of aromatic and unsaturated nitrogen and the reductive elimination chemistry of palladium azolyl and methyleneamido complexes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US, vol. 120, no. 4, 4 February 1998 (1998-02-04), pages 827 - 828, XP002157808 *
PARK K.K. ET AL.: "Synthesis and 1H-nmr of N-arylated nitrogen-containing aromatic heterocycles", BULLETIN OF THE KOREAN CHEMICAL SOCIETY, vol. 6, no. 3, March 1985 (1985-03-01), pages 141 - 144, XP002157810 *
RUSSELL STABLER S. ET AL.: "Preparation of N-arylated heterocycles by nucleophilic aromatic substitution", SYNTHETIC COMMUNICATIONS, MARCEL DEKKER, INC., BASEL, CH, vol. 24, no. 1, 1994, pages 123 - 129, XP000909777, ISSN: 0039-7911 *
SMITH III W.J. & SAWYER J.S.: "A novel and selective method for the N-arylation of indoles mediated by KF/Al2O3", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 37, no. 3, 15 January 1996 (1996-01-15), pages 299 - 302, XP004030349, ISSN: 0040-4039 *
WOLFE J.P. & BUCHWALD S.L.: "Improved functional group compatibility in the palladium-catalyzed amination of aryl bromides", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 38, no. 36, 8 September 1997 (1997-09-08), pages 6359 - 6362, XP004087936, ISSN: 0040-4039 *

Also Published As

Publication number Publication date
JP2002541143A (ja) 2002-12-03
MXPA01009596A (es) 2003-10-14
US20040249185A1 (en) 2004-12-09
CA2360923A1 (en) 2000-10-12
EP1165512A2 (de) 2002-01-02
US6933390B2 (en) 2005-08-23
US6774242B1 (en) 2004-08-10
WO2000059883A2 (de) 2000-10-12
BR0009432A (pt) 2002-01-08
AU3806800A (en) 2000-10-23

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