Literature DB >> 20545313

Intermolecular C-O addition of carboxylic acids to arynes.

Anton V Dubrovskiy1, Richard C Larock.   

Abstract

A novel, efficient, and expedient route to biologically and pharmaceutically important o-hydroxyaryl ketones, xanthones, 4-chromanones, and flavones has been developed starting from readily available carboxylic acids and commercially available o-(trimethylsilyl)aryl triflates.

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Year:  2010        PMID： 20545313      PMCID： PMC2903042          DOI： 10.1021/ol101017z

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


  14 in total

1.  Facile O-arylation of phenols and carboxylic acids.

Authors:  Zhijian Liu; Richard C Larock
Journal:  Org Lett       Date:  2004-01-08       Impact factor: 6.005

Review 2.  Naturally occurring xanthones; latest investigations: isolation, structure elucidation and chemosystematic significance.

Authors:  Hesham R El-Seedi; Dina M H El-Ghorab; Mai A El-Barbary; Mervat F Zayed; Ulf Göransson; Sonny Larsson; Rob Verpoorte
Journal:  Curr Med Chem       Date:  2009       Impact factor: 4.530

3.  Intermolecular C-N addition of amides and S-N addition of sulfinamides to arynes.

Authors:  Zhijian Liu; Richard C Larock
Journal:  J Am Chem Soc       Date:  2005-09-28       Impact factor: 15.419

4.  Synthesis of benzisoxazoles by the [3 + 2] cycloaddition of in situ generated nitrile oxides and arynes.

Authors:  Anton V Dubrovskiy; Richard C Larock
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

5.  The direct acyl-alkylation of arynes.

Authors:  Uttam K Tambar; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2005-04-20       Impact factor: 15.419

6.  A 2:1 coupling reaction of arynes with aldehydes via o-quinone methides: straightforward synthesis of 9-arylxanthenes.

Authors:  Hiroto Yoshida; Masahiko Watanabe; Hiroyuki Fukushima; Joji Ohshita; Atsutaka Kunai
Journal:  Org Lett       Date:  2004-10-28       Impact factor: 6.005

7.  Insertion of benzene rings into the amide bond: one-step synthesis of acridines and acridones from aryl amides.

Authors:  Didier G Pintori; Michael F Greaney
Journal:  Org Lett       Date:  2010-01-01       Impact factor: 6.005

8.  Reaction of benzyne with salicylaldehydes: general synthesis of xanthenes, xanthones, and xanthols.

Authors:  Kentaro Okuma; Akiko Nojima; Nahoko Matsunaga; Kosei Shioji
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

Review 9.  Recent cancer drug development with xanthone structures.

Authors:  Younghwa Na
Journal:  J Pharm Pharmacol       Date:  2009-06       Impact factor: 3.765

10.  Insertion of arynes into carbon-halogen sigma-bonds: regioselective acylation of aromatic rings.

Authors:  Hiroto Yoshida; Yasuhiro Mimura; Joji Ohshita; Atsutaka Kunai
Journal:  Chem Commun (Camb)       Date:  2007-06-21       Impact factor: 6.222
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  11 in total

1.  Synthesis of fluorinated benzophenones, xanthones, acridones, and thioxanthones by iterative nucleophilic aromatic substitution.

Authors:  Zachary R Woydziak; Liqiang Fu; Blake R Peterson
Journal:  J Org Chem       Date:  2011-11-23       Impact factor: 4.354

2.  Synthesis of o-(dimethylamino)aryl ketones and acridones by the reaction of 1,1-dialkylhydrazones and arynes.

Authors:  Anton V Dubrovskiy; Richard C Larock
Journal:  Org Lett       Date:  2011-07-11       Impact factor: 6.005

3.  Palladium-catalyzed annulation of arynes by o-halobenzamides: synthesis of phenanthridinones.

Authors:  Chun Lu; Anton V Dubrovskiy; Richard C Larock
Journal:  J Org Chem       Date:  2012-09-26       Impact factor: 4.354

4.  Synthesis of pyrido[1,2-a]indole malonates and amines through aryne annulation.

Authors:  Donald C Rogness; Nataliya A Markina; Jesse P Waldo; Richard C Larock
Journal:  J Org Chem       Date:  2012-03-06       Impact factor: 4.354

5.  Synthesis of benzisoxazolines by the coupling of arynes with nitrones.

Authors:  Chun Lu; Anton V Dubrovskiy; Richard C Larock
Journal:  J Org Chem       Date:  2012-02-16       Impact factor: 4.354

6.  De novo Assembly of the Benzenoid Ring as a Core Strategy for Synthesis of the Isoindolinone Natural Products Isohericerin, Erinacerin A, and Sterenin A.

Authors:  Chenlong Zhu; Juntian Zhang; Thomas R Hoye
Journal:  Org Lett       Date:  2021-09-20       Impact factor: 6.072

7.  Intermolecular C-O Addition of Carboxylic Acids to Arynes: Synthesis of o-Hydroxyaryl Ketones, Xanthones, 4-Chromanones, and Flavones.

Authors:  Anton V Dubrovskiy; Richard C Larock
Journal:  Tetrahedron       Date:  2013-02-04       Impact factor: 2.457

8.  Formation of acridones by ethylene extrusion in the reaction of arynes with β-lactams and dihydroquinolinones.

Authors:  Yuesi Fang; Donald C Rogness; Richard C Larock; Feng Shi
Journal:  J Org Chem       Date:  2012-07-10       Impact factor: 4.354

9.  Synthesis of o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles by the reaction of hydrazones and arynes.

Authors:  Anton V Dubrovskiy; Richard C Larock
Journal:  J Org Chem       Date:  2012-12-03       Impact factor: 4.354

10.  Nucleophilic addition to 2,3-pyridyne and synthesis of benzonaphthyridinones.

Authors:  Yuesi Fang; Richard C Larock
Journal:  Tetrahedron       Date:  2012-02-09       Impact factor: 2.457
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