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Literature DB >> 20222700

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

Abstract

The reaction of 2-aminoaryl ketones and arynes generated by the treatment of various o-(trimethylsilyl)aryl triflates with CsF results in [4 + 2] annulation to afford substituted acridines in good yields.

Entities: Chemical Disease Gene

Mesh：

Substances：
Acridines
Ketones

Year: 2010 PMID： 20222700 PMCID： PMC2852258 DOI： 10.1021/jo1000687

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

30 in total

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

Authors: Jian Zhao; Richard C Larock
Journal: J Org Chem Date: 2007-01-19 Impact factor: 4.354

2. Evidence for a common non-heme chelatable-iron-dependent activation mechanism for semisynthetic and synthetic endoperoxide antimalarial drugs.

Authors: Paul A Stocks; Patrick G Bray; Victoria E Barton; Mohammed Al-Helal; Michael Jones; Nuna C Araujo; Peter Gibbons; Stephen A Ward; Ruth H Hughes; Giancarlo A Biagini; Jill Davies; Richard Amewu; Amy E Mercer; Gemma Ellis; Paul M O'Neill
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

3. Synthesis and biological activity of stable and potent antitumor agents, aniline nitrogen mustards linked to 9-anilinoacridines via a urea linkage.

Authors: Naval Kapuriya; Kalpana Kapuriya; Xiuguo Zhang; Ting-Chao Chou; Rajesh Kakadiya; Yu-Tse Wu; Tung-Hu Tsai; Yu-Ting Chen; Te-Chang Lee; Anamik Shah; Yogesh Naliapara; Tsann-Long Su
Journal: Bioorg Med Chem Date: 2008-04-15 Impact factor: 3.641

4. A route to regioselectively functionalized carbazoles, dibenzofurans, and dibenzothiophenes through anionic cyclization of benzyne-tethered aryllithiums.

Authors: Roberto Sanz; Yolanda Fernandez; M Pilar Castroviejo; Antonio Pérez; Francisco J Fañanas
Journal: J Org Chem Date: 2006-08-04 Impact factor: 4.354

5. Highly convergent three component benzyne coupling: the total synthesis of ent-clavilactone B.

Authors: Igor Larrosa; Marianne I Da Silva; Patricio M Gómez; Peter Hannen; Eunjung Ko; Steven R Lenger; Simon R Linke; Andrew J P White; Donna Wilton; Anthony G M Barrett
Journal: J Am Chem Soc Date: 2006-11-01 Impact factor: 15.419

6. Novel acridine-based compounds that exhibit an anti-pancreatic cancer activity are catalytic inhibitors of human topoisomerase II.

Authors: Lisa M Oppegard; Andrei V Ougolkov; Doris N Luchini; Renee A Schoon; John R Goodell; Harneet Kaur; Daniel D Billadeau; David M Ferguson; Hiroshi Hiasa
Journal: Eur J Pharmacol Date: 2008-12-03 Impact factor: 4.432

7. Nickel-catalyzed coupling of arynes, alkenes, and boronic acids: dual role of the boronic acid.

Authors: Thiruvellore Thatai Jayanth; Chien-Hong Cheng
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

8. Synthesis and antileishmanial activity of 6-mono-substituted and 3,6-di-substituted acridines obtained by acylation of proflavine.

Authors: Carole Di Giorgio; Kamal Shimi; Gérard Boyer; Florence Delmas; Jean-Pierre Galy
Journal: Eur J Med Chem Date: 2007-03-01 Impact factor: 6.514

9. A one-pot access to 6-substituted phenanthridines from fluoroarenes and nitriles via 1,2-arynes.

Authors: Jan Pawlas; Mikael Begtrup
Journal: Org Lett Date: 2002-08-08 Impact factor: 6.005

10. Tuning of intercalation and electron-transfer processes between DNA and acridinium derivatives through steric effects.

Authors: Joshy Joseph; Elizabeth Kuruvilla; Asha T Achuthan; Danaboyina Ramaiah; Gary B Schuster
Journal: Bioconjug Chem Date: 2004 Nov-Dec Impact factor: 4.774

7 in total

1. An efficient computational model to predict the synthetic utility of heterocyclic arynes.

Authors: Adam E Goetz; Sarah M Bronner; Jordan D Cisneros; Joshua M Melamed; Robert S Paton; K N Houk; Neil K Garg
Journal: Angew Chem Int Ed Engl Date: 2012-02-03 Impact factor: 15.336

2. Facile synthesis of unsymmetrical acridines and phenazines by a Rh(III)-catalyzed amination/cyclization/aromatization cascade.

Authors: Yajing Lian; Joshua R Hummel; Robert G Bergman; Jonathan A Ellman
Journal: J Am Chem Soc Date: 2013-08-19 Impact factor: 15.419

3. Synthesis of heterocycles via Pd-ligand controlled cyclization of 2-chloro-N-(2-vinyl)aniline: preparation of carbazoles, indoles, dibenzazepines, and acridines.

Authors: Dmitry Tsvelikhovsky; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2010-10-13 Impact factor: 15.419