doi: 10.1002/chem.201503496.
Epub 2016 Jan 14.
One-Pot Sequential Propargylation/Cycloisomerization: A Facile [4+2]-Benzannulation Approach to Carbazoles
Affiliations
- PMID: 26836577
- DOI: 10.1002/chem.201503496
Item in Clipboard
One-Pot Sequential Propargylation/Cycloisomerization: A Facile [4+2]-Benzannulation Approach to Carbazoles
Chemistry.
.
Erratum in
-
Corrigendum: One-Pot Sequential Propargylation/Cycloisomerization: A Facile [4+2]-Benzannulation Approach to Carbazoles.Chemistry. 2016 Dec 12;22(50):17888. doi: 10.1002/chem.201605089. Epub 2016 Nov 15. Chemistry. 2016. PMID: 27935205 No abstract available.
Abstract
A novel one-pot [4+2]-benzannulation approach to substituted carbazoles is accomplished by acid-catalyzed C3-propargylation of 2-alkenyl/aryl indoles with 1-aryl propargylic alcohols, followed by cycloisomerization. A variety of 2-alkenylated indoles and 2-aryl/heteroaryl indoles successfully participated in this tandem reaction with 1-aryl/heteroaryl propargylic alcohols to provide diversely substituted and annulated carbazoles, as well as an aza[5]helicene.
Keywords: benzannulation; carbazoles; cycloisomerization; metal-free synthesis; propargylation.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Similar articles
-
[4 + 2] Benzannulation of 3-Alkenylpyrroles/Thiophenes with Propargylic Alcohols: Access to Substituted Indoles, Benzothiophenes, and Aza[5]helicenes.J Org Chem. 2017 Mar 3;82(5):2345-2354. doi: 10.1021/acs.joc.6b02637. Epub 2017 Feb 22. J Org Chem. 2017. PMID: 28195471
-
Brønsted acid-catalyzed propargylation/cycloisomerization tandem reaction: one-pot synthesis of substituted oxazoles from propargylic alcohols and amides.J Org Chem. 2009 Apr 17;74(8):3148-51. doi: 10.1021/jo8027533. J Org Chem. 2009. PMID: 19354325
-
Corrigendum: One-Pot Sequential Propargylation/Cycloisomerization: A Facile [4+2]-Benzannulation Approach to Carbazoles.Chemistry. 2016 Dec 12;22(50):17888. doi: 10.1002/chem.201605089. Epub 2016 Nov 15. Chemistry. 2016. PMID: 27935205 No abstract available.
-
One-Pot Synthesis of N-Fused Benzimidazo-β-carbolines through Sequential Propargylation/aza-Cycloisomerization Approach.J Org Chem. 2024 Feb 16;89(4):2675-2682. doi: 10.1021/acs.joc.3c02702. Epub 2024 Feb 6. J Org Chem. 2024. PMID: 38319121
-
C3-C3' and C6-C6' Oxidative Couplings of Carbazoles.Chemistry. 2019 Jan 24;25(5):1142-1151. doi: 10.1002/chem.201803246. Epub 2018 Nov 19. Chemistry. 2019. PMID: 30191617 Review.
Cited by
-
Recent Advances in the Synthesis of Propargyl Derivatives, and Their Application as Synthetic Intermediates and Building Blocks.Molecules. 2023 Apr 11;28(8):3379. doi: 10.3390/molecules28083379. Molecules. 2023. PMID: 37110613 Free PMC article. Review.
-
Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration.ACS Omega. 2018 Nov 7;3(11):15024-15034. doi: 10.1021/acsomega.8b02393. eCollection 2018 Nov 30. ACS Omega. 2018. PMID: 31458169 Free PMC article.
-
Recent advances in metal-free catalysts for the synthesis of N-heterocyclic frameworks focusing on 5- and 6-membered rings: a review.RSC Adv. 2025 Mar 31;15(13):9676-9755. doi: 10.1039/d5ra00962f. eCollection 2025 Mar 28. RSC Adv. 2025. PMID: 40165917 Free PMC article. Review.
-
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.
Publication types
LinkOut - more resources
Full Text Sources
Other Literature Sources
Miscellaneous
