Literature DB >> 17221977

Synthesis of xanthones, thioxanthones, and acridones by the coupling of arynes and substituted benzoates.

Jian Zhao1, Richard C Larock.   

Abstract

The reaction of silylaryl triflates, CsF, and ortho-heteroatom-substituted benzoates affords a general and efficient way to prepare biologically interesting xanthones, thioxanthones, and acridones. This chemistry presumably proceeds by a tandem intermolecular nucleophilic coupling of the benzoate with an aryne and a subsequent intramolecular electrophilic cyclization.

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Year:  2007        PMID： 17221977      PMCID： PMC2529457          DOI： 10.1021/jo0620718

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  21 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

2.  Automated protein structure determination from NMR spectra.

Authors:  Blanca López-Méndez; Peter Güntert
Journal:  J Am Chem Soc       Date:  2006-10-11       Impact factor: 15.419

3.  Xanthones as inhibitors of growth of human cancer cell lines and their effects on the proliferation of human lymphocytes in vitro.

Authors:  Madalena Pedro; Fátima Cerqueira; Maria Emília Sousa; Maria São José Nascimento; Madalena Pinto
Journal:  Bioorg Med Chem       Date:  2002-12       Impact factor: 3.641

4.  Palladium-catalyzed cross-coupling reactions in total synthesis.

Authors:  K C Nicolaou; Paul G Bulger; David Sarlah
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-18       Impact factor: 15.336

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.  Synthesis and evaluation of acridine- and acridone-based anti-herpes agents with topoisomerase activity.

Authors:  John R Goodell; Avni A Madhok; Hiroshi Hiasa; David M Ferguson
Journal:  Bioorg Med Chem       Date:  2006-05-19       Impact factor: 3.641

7.  Xanthone derivatives from Cratoxylum cochinchinense roots.

Authors:  W Mahabusarakam; W Nuangnaowarat; W C Taylor
Journal:  Phytochemistry       Date:  2005-11-28       Impact factor: 4.072

8.  Preferential target is mitochondria in alpha-mangostin-induced apoptosis in human leukemia HL60 cells.

Authors:  Kenji Matsumoto; Yukihiro Akao; Hong Yi; Kenji Ohguchi; Tetsuro Ito; Toshiyuki Tanaka; Emi Kobayashi; Munekazu Iinuma; Yoshinori Nozawa
Journal:  Bioorg Med Chem       Date:  2004-11-15       Impact factor: 3.641

9.  A convenient route to diverse heterocycles through an addition of beta-amino carbonyl compounds to 3-halogeno-4-methoxybenzynes.

Authors:  Kyongho Yoon; Sung Min Ha; Kyongtae Kim
Journal:  J Org Chem       Date:  2005-07-08       Impact factor: 4.354

10.  HIV-1 neutralization and tumor cell proliferation inhibition in vitro by simplified analogues of pyrido[4,3,2-mn]thiazolo[5,4-b]acridine marine alkaloids.

Authors:  I B Taraporewala; J W Cessac; T C Chanh; A V Delgado; R F Schinazi
Journal:  J Med Chem       Date:  1992-07-24       Impact factor: 7.446
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  14 in total

1.  Synthesis of acridines by the [4 + 2] annulation of arynes and 2-aminoaryl ketones.

Authors:  Donald C Rogness; Richard C Larock
Journal:  J Org Chem       Date:  2010-04-02       Impact factor: 4.354

2.  Synthesis of 9-Substituted Xanthenes by the Condensation of Arynes with ortho-Hydroxychalcones.

Authors:  Chun Lu; Anton V Dubrovskiy; Richard C Larock
Journal:  Tetrahedron Lett       Date:  2012-02-25       Impact factor: 2.415

3.  Synthesis of dihydrobenzisoxazoles by the [3 + 2] cycloaddition of arynes and oxaziridines.

Authors:  Arif Kivrak; Richard C Larock
Journal:  J Org Chem       Date:  2010-11-05       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.  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

7.  Copper-catalyzed ortho-acylation of phenols with aryl aldehydes and its application in one-step preparation of xanthones.

Authors:  Jun Hu; Enoch A Adogla; Yong Ju; Daping Fan; Qian Wang
Journal:  Chem Commun (Camb)       Date:  2012-10-15       Impact factor: 6.222

8.  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

9.  Benzyne click chemistry: synthesis of benzotriazoles from benzynes and azides.

Authors:  Feng Shi; Jesse P Waldo; Yu Chen; Richard C Larock
Journal:  Org Lett       Date:  2008-05-14       Impact factor: 6.005

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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