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WO2012073038A3 - Composés et leurs procédés de préparation - Google Patents

Composés et leurs procédés de préparation Download PDF

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Publication number
WO2012073038A3
WO2012073038A3 PCT/GB2011/052381 GB2011052381W WO2012073038A3 WO 2012073038 A3 WO2012073038 A3 WO 2012073038A3 GB 2011052381 W GB2011052381 W GB 2011052381W WO 2012073038 A3 WO2012073038 A3 WO 2012073038A3
Authority
WO
WIPO (PCT)
Prior art keywords
boronic acid
derivative
transition metal
cyclobutenone
formula
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/GB2011/052381
Other languages
English (en)
Other versions
WO2012073038A2 (fr
Inventor
Joseph Patrick Anthony Harrity
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AUVINET ANNE-LAURE
University of Sheffield
Original Assignee
AUVINET ANNE-LAURE
University of Sheffield
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 AUVINET ANNE-LAURE, University of Sheffield filed Critical AUVINET ANNE-LAURE
Publication of WO2012073038A2 publication Critical patent/WO2012073038A2/fr
Publication of WO2012073038A3 publication Critical patent/WO2012073038A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
    • C07B37/04—Substitution
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
    • C07B37/10—Cyclisation
    • C07B37/12—Diels-Alder reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • C07C49/784—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with all keto groups bound to a non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds

Landscapes

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

Abstract

La présente invention a pour objet un procédé de préparation d'un phénol d'acide ortho- et/ou méta-boronique ou d'un dérivé d'un tel acide boronique comprenant les étapes consistant : à faire réagir une cyclobuténone avec un acide alcynylboronique ou son dérivé en présence d'un catalyseur de type complexe d'oléfine et de métal de transition. La présente invention concerne également un composé ayant la structure de Formule (Ia) ou de Formule (Ib) : (Ia) (Ib) dans lesquelles R1, R2, R3 et R4 sont chacun indépendamment choisis dans le groupe comprenant : H et un substituant et R est un acide boronique ou son dérivé et un composé ayant la structure de Formule (IIa) ou de Formule (IIb) : (IIa) (IIb) dans lesquelles R1, R2 et R4 sont chacun indépendamment choisis dans le groupe comprenant : H et un substituant et R est un acide boronique ou son dérivé. ²De plus, la présente invention concerne des produits ou des compositions de matière comprenant des composés ayant la structure de Formule (Ia), (Ib), (IIa) ou (IIb) et une quantité détectable d'un métal de transition, ainsi qu'une banque de composés comprenant au moins deux composés selon l'invention, un procédé de préparation d'un ortho- et/ou méta-arylphénol comprenant les étapes consistant : à faire réagir une cyclobuténone avec un acide alcynylboronique ou son dérivé en présence d'un catalyseur de type complexe d'oléfine et de métal de transition et un partenaire de couplage croisé aryle, et un procédé de préparation d'un ortho- et/ou méta-arylphénol comprenant les étapes consistant : à faire réagir un phénol d'acide ortho- et/ou méta-boronique ou son dérivé avec un partenaire de couplage croisé aryle.
PCT/GB2011/052381 2010-12-01 2011-12-01 Composés et leurs procédés de préparation Ceased WO2012073038A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1020357.8 2010-12-01
GB1020357.8A GB2486631A (en) 2010-12-01 2010-12-01 Phenol/quinone boronic acids/esters and method of preparation thereof

Publications (2)

Publication Number Publication Date
WO2012073038A2 WO2012073038A2 (fr) 2012-06-07
WO2012073038A3 true WO2012073038A3 (fr) 2012-07-19

Family

ID=43500928

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2011/052381 Ceased WO2012073038A2 (fr) 2010-12-01 2011-12-01 Composés et leurs procédés de préparation

Country Status (2)

Country Link
GB (1) GB2486631A (fr)
WO (1) WO2012073038A2 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101572521B1 (ko) * 2013-09-02 2015-11-27 고려대학교 산학협력단 히드록시아렌 붕소산 화합물의 열적 탈붕소수소화 및 이를 이용하여 페놀계 화합물의 오르소 또는 메타 위치에 작용기를 도입시킨 히드록시아렌 화합물의 제조방법
FR3040169B1 (fr) * 2015-08-20 2017-08-25 Ecole Superieure Physique & Chimie Ind Ville De Paris Procede de preparation d'une librairie de composes
CN114181048B (zh) * 2021-12-20 2024-06-21 宁夏清研高分子新材料有限公司 一种高产率的4-氟联苯酚的制备方法

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060089405A1 (en) * 2004-10-21 2006-04-27 Wyeth Asymmetric synthesis of dihydrobenzofuran derivatives
US20060167049A1 (en) * 2002-04-11 2006-07-27 Francis Barth Terphenly derivatives, preparation thereof, compositions containing same
WO2008038955A1 (fr) * 2006-09-27 2008-04-03 Chong Kun Dang Pharmaceutical Corp. Dérivé de benzophénone convenant pour inhiber la formation de microtubule
WO2009010139A2 (fr) * 2007-07-13 2009-01-22 Merck Patent Gmbh Dérivés de quinazolinamide
US20090076268A1 (en) * 2007-09-14 2009-03-19 Fitzgerald Anne E Facile assembly of fused benzofuro-heterocycles
WO2010015652A2 (fr) * 2008-08-07 2010-02-11 Smithkline Beecham Corporation Composés thiazole utilisés comme activateurs de la guanylate cyclase soluble
US20100216764A1 (en) * 2009-02-26 2010-08-26 Kim Ronald M Soluble Guanylate Cyclase Activators
WO2011029855A1 (fr) * 2009-09-10 2011-03-17 Glaxosmithkline Llc Dérivés pyrrolo-pyridine utilisés comme activateurs de l'ampk
WO2011040963A1 (fr) * 2009-09-30 2011-04-07 Massachusetts Institute Of Technology Métathèse d'oléfines hautement sélective vis-à-vis des z

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006039423A1 (de) * 2006-08-23 2008-02-28 Werner, Johannes Halbleitende Polyaddukte mit kolumnarer Struktur
EP2008991A1 (fr) * 2007-06-29 2008-12-31 Bayer CropScience AG Procédé destiné à la fabrication de bi-aryles
WO2009108670A1 (fr) * 2008-02-28 2009-09-03 Merck Serono S.A. Inhibiteurs de protéine kinase et leur utilisation

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060167049A1 (en) * 2002-04-11 2006-07-27 Francis Barth Terphenly derivatives, preparation thereof, compositions containing same
US20060089405A1 (en) * 2004-10-21 2006-04-27 Wyeth Asymmetric synthesis of dihydrobenzofuran derivatives
WO2008038955A1 (fr) * 2006-09-27 2008-04-03 Chong Kun Dang Pharmaceutical Corp. Dérivé de benzophénone convenant pour inhiber la formation de microtubule
WO2009010139A2 (fr) * 2007-07-13 2009-01-22 Merck Patent Gmbh Dérivés de quinazolinamide
US20090076268A1 (en) * 2007-09-14 2009-03-19 Fitzgerald Anne E Facile assembly of fused benzofuro-heterocycles
WO2010015652A2 (fr) * 2008-08-07 2010-02-11 Smithkline Beecham Corporation Composés thiazole utilisés comme activateurs de la guanylate cyclase soluble
US20100216764A1 (en) * 2009-02-26 2010-08-26 Kim Ronald M Soluble Guanylate Cyclase Activators
WO2011029855A1 (fr) * 2009-09-10 2011-03-17 Glaxosmithkline Llc Dérivés pyrrolo-pyridine utilisés comme activateurs de l'ampk
WO2011040963A1 (fr) * 2009-09-30 2011-04-07 Massachusetts Institute Of Technology Métathèse d'oléfines hautement sélective vis-à-vis des z

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
ANNE-LAURE AUVINET ET AL: "A Nickel-Catalyzed Benzannulation Approach to Aromatic Boronic Esters", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 50, no. 12, 21 February 2011 (2011-02-21), pages 2769 - 2772, XP055017240, ISSN: 1433-7851, DOI: 10.1002/anie.201007598 *
CAO ET AL: "The design and preliminary structure-activity relationship studies of benzotriazines as potent inhibitors of Abl and Abl-T315I enzymes", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, PERGAMON, ELSEVIER SCIENCE, GB, vol. 17, no. 21, 1 November 2007 (2007-11-01), pages 5812 - 5818, XP022267178, ISSN: 0960-894X, DOI: 10.1016/J.BMCL.2007.08.043 *
CRAIG A. MERLIC ET AL: "Cyclization reactions of chromium dienylcarbene complexes. Entry to ortho-substituted aromatic alcohols via a designed photoreaction", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 113, no. 19, 1 September 1991 (1991-09-01), pages 7418 - 7420, XP055017540, ISSN: 0002-7863, DOI: 10.1021/ja00019a047 *
DELANEY P M ET AL: "A 2-pyrone cycloaddition route to functionalised aromatic boronic esters", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 64, no. 5, 28 January 2008 (2008-01-28), pages 866 - 873, XP025770104, ISSN: 0040-4020, [retrieved on 20071024], DOI: 10.1016/J.TET.2007.08.118 *
DI QIU ET AL: "Gold(III)-Catalyzed Halogenation of Aromatic Boronates with N -Halosuccinimides", ORGANIC LETTERS, vol. 12, no. 23, 11 November 2010 (2010-11-11), pages 5474 - 5477, XP055017482, ISSN: 1523-7060, DOI: 10.1021/ol102350v *
HELMUT MACK ET AL: "A pyridine dialkoxide titanium dichloride complex. Synthesis and molecular structure of 2,6-bis(2,2-diphenyl-2-trimethylsilyloxy- ethyl)pyridine", JOURNAL OF THE CHEMICAL SOCIETY, DALTON TRANSACTIONS, no. 6, 1 January 1998 (1998-01-01), pages 917 - 922, XP055017580, ISSN: 0300-9246, DOI: 10.1039/a708041g *
MARCOS VEGUILLAS ET AL: "Synthesis of Benzo- and Naphthoquinonyl Boronic Acids: Exploring the Diels-Alder Reactivity", CHEMISTRY - A EUROPEAN JOURNAL, vol. 16, no. 12, 22 March 2010 (2010-03-22), pages 3707 - 3719, XP055017505, ISSN: 0947-6539, DOI: 10.1002/chem.200902796 *
MARK A. HUFFMAN ET AL: "Nickel(0)-catalyzed synthesis of substituted phenols from cyclobutenones and alkynes", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 113, no. 7, 1 March 1991 (1991-03-01), pages 2771 - 2772, XP055017315, ISSN: 0002-7863, DOI: 10.1021/ja00007a072 *
SCOT H. BODNAR ET AL, CHEMICAL COMMUNICATIONS, no. 20, 11 October 2001 (2001-10-11), pages 2150 - 2151, XP055017529, ISSN: 1359-7345, DOI: 10.1039/b106192p *
TAKASHI IKAWA ET AL: "Preparation and Regioselective Diels-Alder Reactions of Borylbenzynes: Synthesis of Functionalized Arylboronates", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 49, no. 32, 26 July 2010 (2010-07-26), pages 5563 - 5566, XP055017375, ISSN: 1433-7851, DOI: 10.1002/anie.201002191 *

Also Published As

Publication number Publication date
GB201020357D0 (en) 2011-01-12
GB2486631A (en) 2012-06-27
WO2012073038A2 (fr) 2012-06-07

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