Recent advances in the synthesis of carbazoles from indoles
- PMID: 31497833
- DOI: 10.1039/c9ob01381d
Recent advances in the synthesis of carbazoles from indoles
Abstract
Carbazoles are privileged nitrogen heterocycles that are present in a wide range of natural products, pharmaceuticals, and functional materials. Due to their wide application, various synthetic strategies are available in the literature using substituted amines or indoles as a substrate. Thus, this review comprehensively highlights the (2015-2019) article that focuses on the synthesis of carbazoles derived from an indole-template through transition-metal catalyzed C-H functionalization, metal-free cyclization, three-component reaction, and electrophilic iodocyclizations. The synthetic strategies described in this review provided diversely substituted carbazoles and few of them have profound pharmacological activity.
Similar articles
-
Synthesis of substituted indoline and carbazole by benzyne-mediated cyclization-functionalization.Org Lett. 2013 Apr 19;15(8):1946-9. doi: 10.1021/ol400597f. Epub 2013 Apr 2. Org Lett. 2013. PMID: 23547831
-
An efficient synthesis of indolo[3,2-a]carbazoles via the novel acid catalyzed reaction of indoles and diaryl-1,2-diones.Org Biomol Chem. 2008 May 21;6(10):1738-42. doi: 10.1039/b803009j. Epub 2008 Apr 8. Org Biomol Chem. 2008. PMID: 18452007
-
Gold-catalyzed cyclization of 1-(indol-3-yl)-3-alkyn-1-ols: facile synthesis of diversified carbazoles.Chemistry. 2013 Aug 5;19(32):10625-31. doi: 10.1002/chem.201301203. Epub 2013 Jul 10. Chemistry. 2013. PMID: 23843184
-
Catalytic asymmetric synthesis of tetrahydrocarbazoles.Chem Commun (Camb). 2019 May 28;55(44):6151-6164. doi: 10.1039/c9cc02486g. Chem Commun (Camb). 2019. PMID: 31093637 Review.
-
[Synthetic studies on natural products with aromatic nitrogen heterocycles based on development of the methods for the formation of aryl carbon-nitrogen bond].Yakugaku Zasshi. 2013;133(10):1065-78. doi: 10.1248/yakushi.13-00189. Yakugaku Zasshi. 2013. PMID: 24088350 Review. Japanese.
Cited by
-
Structural diversity-guided optimization of carbazole derivatives as potential cytotoxic agents.Front Chem. 2023 Jan 18;11:1104868. doi: 10.3389/fchem.2023.1104868. eCollection 2023. Front Chem. 2023. PMID: 36742033 Free PMC article.
-
Synthesis of 4-Hydroxycarbazole Derivatives by Benzannulation of 3-Nitroindoles with Alkylidene Azlactones.ACS Omega. 2021 Jun 25;6(26):16969-16979. doi: 10.1021/acsomega.1c01992. eCollection 2021 Jul 6. ACS Omega. 2021. PMID: 34250355 Free PMC article.
-
Recent synthetic strategies for the construction of functionalized carbazoles and their heterocyclic motifs enabled by Lewis acids.RSC Adv. 2023 Nov 6;13(46):32596-32626. doi: 10.1039/d3ra06396h. eCollection 2023 Oct 31. RSC Adv. 2023. PMID: 37936643 Free PMC article. Review.
-
Synthesis of indoles, indolines, and carbazoles via palladium-catalyzed C─H activation.Green Synth Catal. 2021 May;2(2):216-227. doi: 10.1016/j.gresc.2021.02.001. Epub 2021 Mar 4. Green Synth Catal. 2021. PMID: 36267892 Free PMC article.
-
One-Pot Synthesis of 2-Substituted Indoles and 7-Azaindoles via Sequential Alkynylation and Cyclization of 2-Iodo-N-mesylarylamines and Alkynes in the Presence of Cu2O.Asian J Org Chem. 2025 Jan;14(1):e202400421. doi: 10.1002/ajoc.202400421. Epub 2024 Nov 19. Asian J Org Chem. 2025. PMID: 39830603 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources