Synthesis of acridines by the [4 + 2] annulation of arynes and 2-aminoaryl ketones
- PMID: 20222700
- PMCID: PMC2852258
- DOI: 10.1021/jo1000687
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.
Similar articles
-
Synthesis of o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles by the reaction of hydrazones and arynes.J Org Chem. 2012 Dec 21;77(24):11232-56. doi: 10.1021/jo302378w. Epub 2012 Dec 3. J Org Chem. 2012. PMID: 23206164 Free PMC article.
-
Synthesis of xanthones, thioxanthones, and acridones by the coupling of arynes and substituted benzoates.J Org Chem. 2007 Jan 19;72(2):583-8. doi: 10.1021/jo0620718. J Org Chem. 2007. PMID: 17221977 Free PMC article.
-
Cascade nucleophilic addition-cyclic Michael addition of arynes and phenols/anilines bearing ortho alpha,beta-unsaturated groups: facile synthesis of 9-functionalized xanthenes/acridines.J Org Chem. 2010 Jan 15;75(2):506-9. doi: 10.1021/jo902311a. J Org Chem. 2010. PMID: 20020766
-
[The structural and functional analysis of the biological activity of acridine derivatives].Vestn Ross Akad Med Nauk. 2004;(2):29-34. Vestn Ross Akad Med Nauk. 2004. PMID: 15101206 Review. Russian.
-
Exploring the therapeutic potential of acridines: Synthesis, structure, and biological applications.Bioorg Chem. 2025 Feb;155:108096. doi: 10.1016/j.bioorg.2024.108096. Epub 2024 Dec 27. Bioorg Chem. 2025. PMID: 39756205 Review.
Cited by
-
Facile synthesis of unsymmetrical acridines and phenazines by a Rh(III)-catalyzed amination/cyclization/aromatization cascade.J Am Chem Soc. 2013 Aug 28;135(34):12548-51. doi: 10.1021/ja406131a. Epub 2013 Aug 19. J Am Chem Soc. 2013. PMID: 23957711 Free PMC article.
-
Nucleophilic addition to 2,3-pyridyne and synthesis of benzonaphthyridinones.Tetrahedron. 2012 Apr 1;68(13):2819-2826. doi: 10.1016/j.tet.2012.02.002. Epub 2012 Feb 9. Tetrahedron. 2012. PMID: 23519554 Free PMC article.
-
An efficient computational model to predict the synthetic utility of heterocyclic arynes.Angew Chem Int Ed Engl. 2012 Mar 12;51(11):2758-62. doi: 10.1002/anie.201108863. Epub 2012 Feb 3. Angew Chem Int Ed Engl. 2012. PMID: 22307724 Free PMC article.
-
Synthesis of heterocycles via Pd-ligand controlled cyclization of 2-chloro-N-(2-vinyl)aniline: preparation of carbazoles, indoles, dibenzazepines, and acridines.J Am Chem Soc. 2010 Oct 13;132(40):14048-51. doi: 10.1021/ja107511g. J Am Chem Soc. 2010. PMID: 20858012 Free PMC article.
-
1,3- and 1,4-Benzdiyne equivalents for regioselective synthesis of polycyclic heterocycles.Chem Sci. 2016 Aug 1;7(8):5206-5211. doi: 10.1039/c6sc00798h. Epub 2016 Apr 18. Chem Sci. 2016. PMID: 30155171 Free PMC article.
References
-
- Chen Y, Larock RC. In: Modern Arylation Methods. Ackerman J, editor. Wiley/VCH; New York: 2009. p. 401.
-
- Beller MA, Breindl C, Riermeier TH, Tillack A. J Org Chem. 2001;66:1403. - PubMed
-
- Huang XC, Liu YL, Liang Y, Pi SF, Wang F, Li JH. Org Lett. 2008;10:1525. - PubMed
-
- Dixon S, Wang X, Lam KS, Kurth MJ. Tetrahedron Lett. 2005;46:7443.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources