Rh-Catalyzed Synthesis of Cyclopenta[]carbazoles via Cascade C-H/C-C Bond Cleavage and Cyclization Reactions: Using Amide as a Traceless Directing Group.

Org Lett

State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry , Nankai University, Tianjin 300071 , People's Republic of China.

Published: January 2020

Rhodium-catalyzed cascade C-H/C-C cleavage and cyclization reactions of 3-amide substituted indoles with diynes to construct cyclopenta[]carbazoles have been developed. A strategy amide worked as a novel traceless directing group along with C-C bond cleavage via Friedel-Crafts-retro reaction has been disclosed in this protocol. This method exhibits a broad substrate scope and tolerates various functional groups, furnishing the carbazole derivatives in good to high yields.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.9b03969DOI Listing

Publication Analysis

Top Keywords

cascade c-h/c-c
8
bond cleavage
8
cleavage cyclization
8
cyclization reactions
8
traceless directing
8
directing group
8
rh-catalyzed synthesis
4
synthesis cyclopenta[]carbazoles
4
cyclopenta[]carbazoles cascade
4
c-h/c-c bond
4

Similar Publications

Synthesis of CF-Azafluorenes through the Cascade Reaction of 2-Imidazoles with CF-Ynones.

Org Lett

December 2024

State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.

Article Synopsis
  • - A new method for creating trifluoromethyl-substituted azafluorenes is introduced, involving the reaction of 5-aryl-2-imidazoles with CF-ynones.
  • - The reaction features a unique process that starts with C-H activation and leads to the formation of a spiro intermediate, which then undergoes further transformations to form the final azafluorene derivatives.
  • - The synthesized compounds exhibit potential cancer-fighting properties, demonstrating their effectiveness against certain cancer cell lines.
View Article and Find Full Text PDF

A straightforward approach to synthesise isocoumarins Rh(III)-catalyzed C-H/C-C bond activation/annulation cascade of enaminones and iodonium ylides has been explored. The established protocol is characterized by an exceedingly simple reaction system, high regioselectivity and good functional group tolerance. Moreover, this strategy may provide a new route to cleavage of the C(sp)-C(O) bond of unstrained ketones.

View Article and Find Full Text PDF

A Rh-catalyzed weak chelation-guided C4-alkylation of indoles has been accomplished using cyclopropanols as an alkylating agent via the cascade C-H and C-C bond activation. The substrate scope, functional group tolerance, and late-stage mutation of drug molecules are the important practical features.

View Article and Find Full Text PDF

Ru(II)-Catalyzed Tunable Cascade Reaction C-H/C-C Bond Cleavage.

J Org Chem

October 2020

Department Engineering Research Centre of Molecular Medicine of Ministry of Education, Key Laboratory of Fujian Molecular Medicine, Key Laboratory of Xiamen Marine and Gene Drugs, Key Laboratory of Precision Medicine and Molecular Diagnosis of Fujian Universities, School of Biomedical Sciences, Huaqiao University, Xiamen 361021, P. R. China.

A facile synthesis of various 3-(alkoxyalkyl)-1-indoles from pyrazolidinones, 2-acetylenic ketones, and alkyl alcohols C-H/C-C bond activation has been developed. The reaction proceeds smoothly under the proper reaction conditions, and preliminary mechanistic studies suggest that NaOAc is crucial for C-C bond activation. The advantages of the present method represent a redox-neutral process and exhibit excellent chemo and regioselectivity.

View Article and Find Full Text PDF

Rh-Catalyzed Synthesis of Cyclopenta[]carbazoles via Cascade C-H/C-C Bond Cleavage and Cyclization Reactions: Using Amide as a Traceless Directing Group.

Org Lett

January 2020

State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry , Nankai University, Tianjin 300071 , People's Republic of China.

Rhodium-catalyzed cascade C-H/C-C cleavage and cyclization reactions of 3-amide substituted indoles with diynes to construct cyclopenta[]carbazoles have been developed. A strategy amide worked as a novel traceless directing group along with C-C bond cleavage via Friedel-Crafts-retro reaction has been disclosed in this protocol. This method exhibits a broad substrate scope and tolerates various functional groups, furnishing the carbazole derivatives in good to high yields.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!