Literature DB >> 17348665

Rapid and efficient microwave-assisted copper(0)-catalyzed ullmann coupling reaction: general access to anilinoanthraquinone derivatives.

Younis Baqi1, Christa E Müller.   

Abstract

[structure: see text]. The synthesis of anilinoanthraquinones 3a-z was achieved by a new, Cu(0)-catalyzed, microwave-assisted Ullmann coupling reaction of bromaminic acid (1) with aniline derivatives 2a-z in phosphate buffer. Good to excellent isolated yields were obtained within only 2-20 min at 80-120 degrees C and 40-100 W. The new procedure provides the first general access to anilinoanthraquinones, furnishing a number of previously inaccessible compounds. It is superior to classical methods in all aspects, including yields, reaction time, and versatility.

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Year:  2007        PMID: 17348665     DOI: 10.1021/ol070102v

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  10 in total

1.  Correction to Anthraquinone Derivatives as Potent Inhibitors of c-Met Kinase and the Extracellular Signaling Pathway.

Authors:  Zhongjie Liang; Jing Ai; Xiao Ding; Xia Peng; Dengyou Zhang; Ruihan Zhang; Ying Wang; Fang Liu; Mingyue Zheng; Hualiang Jiang; Hong Liu; Meiyu Geng; Cheng Luo
Journal:  ACS Med Chem Lett       Date:  2014-12-15       Impact factor: 4.345

2.  Synthesis of alkyl- and aryl-amino-substituted anthraquinone derivatives by microwave-assisted copper(0)-catalyzed Ullmann coupling reactions.

Authors:  Younis Baqi; Christa E Müller
Journal:  Nat Protoc       Date:  2010-04-29       Impact factor: 13.491

3.  Structure-activity relationships of anthraquinone derivatives derived from bromaminic acid as inhibitors of ectonucleoside triphosphate diphosphohydrolases (E-NTPDases).

Authors:  Younis Baqi; Stefanie Weyler; Jamshed Iqbal; Herbert Zimmermann; Christa E Müller
Journal:  Purinergic Signal       Date:  2008-06-05       Impact factor: 3.765

4.  Microwave-assisted synthesis of macrocycles via intramolecular and/or bimolecular Ullmann coupling.

Authors:  Li Shen; Charles J Simmons; Dianqing Sun
Journal:  Tetrahedron Lett       Date:  2012-06-06       Impact factor: 2.415

5.  RECENT SYNTHETIC DEVELOPMENTS AND APPLICATIONS OF THE ULLMANN REACTION. A REVIEW.

Authors:  Hao Lin; Dianqing Sun
Journal:  Org Prep Proced Int       Date:  2013       Impact factor: 1.628

6.  Convergent synthesis of the potent P2Y receptor antagonist MG 50-3-1 based on a regioselective Ullmann coupling reaction.

Authors:  Younis Baqi; Christa E Müller
Journal:  Molecules       Date:  2012-03-05       Impact factor: 4.411

7.  Synthesis and Spectral Properties of 8-Anilinonaphthalene-1-sulfonic Acid (ANS) Derivatives Prepared by Microwave-Assisted Copper(0)-Catalyzed Ullmann Reaction.

Authors:  Nan Wang; Erik B Faber; Gunda I Georg
Journal:  ACS Omega       Date:  2019-10-28

8.  Central P2Y12 receptor blockade alleviates inflammatory and neuropathic pain and cytokine production in rodents.

Authors:  Gergely Horváth; Flóra Gölöncsér; Cecilia Csölle; Kornél Király; Rómeó D Andó; Mária Baranyi; Bence Koványi; Zoltán Máté; Kristina Hoffmann; Irina Algaier; Younis Baqi; Christa E Müller; Ivar Von Kügelgen; Beáta Sperlágh
Journal:  Neurobiol Dis       Date:  2014-06-25       Impact factor: 5.996

9.  Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) - precursors for dyes and drugs.

Authors:  Enas M Malik; Younis Baqi; Christa E Müller
Journal:  Beilstein J Org Chem       Date:  2015-11-26       Impact factor: 2.883

10.  1-Hydroxyanthraquinones Containing Aryl Substituents as Potent and Selective Anticancer Agents.

Authors:  Nafisa S Sirazhetdinova; Victor A Savelyev; Tatyana S Frolova; Dmitry S Baev; Lyubov S Klimenko; Ivan V Chernikov; Olga S Oleshko; Teresa A Sarojan; Andrey G Pokrovskii; Elvira E Shults
Journal:  Molecules       Date:  2020-05-29       Impact factor: 4.411

  10 in total

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