Five-membered ring systems: Pyrroles and benzo analogs DOI
Chuan Shan, Justin M. Lopchuk

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 123 - 173

Published: Jan. 1, 2024

Language: Английский

TMSOTf-Promoted Cyclization of Indole-2-methyl-α-aminoketones: Access to 4-Aryl-Substituted β-Carbolines DOI
Xinyu Yang, Jin‐Ming Yang, Bin Wu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(5), P. 1105 - 1109

Published: Jan. 30, 2024

An efficient method to construct 4-aryl-substituted β-carbolines from indole-2-methyl-α-aminoketones via a TMSOTf-promoted annulation reaction was reported. High yield along with wide substrate scope and functional group tolerance make this applicable build various highly potential bioactive β-carboline derivatives.

Language: Английский

Citations

3
Synthesis of Highly Fluorescent Thiazole Fused Benzo[a] Carbazoles by Sunlight Driven Photocyclization of Indolylthiazoles DOI Creative Commons

Prabhas Bhaumick,

Nurabul Mondal,

Lokman H. Choudhury

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 19, 2024

Abstract Herein we report for the first time a sunlight‐driven, irreversible photocyclization reaction of indole‐linked trisubstituted thiazoles, synthesis highly fluorescent thiazole‐fused benzo[ ]carbazoles using mixture solvents (CH 3 CN: DMSO; : 1). Ring opening indole moiety was observed in case thiazole derivatives having 2‐methyl substituents. Under similar conditions, thiazoles cyclic 1,3‐dicarbonyls place also worked. This provides products two medicinally important moieties and benzocarbazoles. We have studied photophysical properties all found that most synthesized very good fluorescence quantum yields.

Language: Английский

Citations

3
Visible Light-Induced Cascade Phosphorylation/Cyclization to Access Phosphorus-Containing Diazocinocarbazoles DOI
Yifan Yin, Fei Liu, Miao Tian

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 16, 2025

Herein, we developed a novel radical cascade phosphorylation/cyclization strategy to access phosphorus-containing diazocine-fused carbazoles in moderate good yields, offering expanded opportunities for the exploration of biologically active molecules. This method features metal-free photochemical tandem, mild conditions, broad substrate scopes, and scale-up ability. Mechanistic experiments implied that this photocatalyzed reaction was realized by sequence EnT/SET/SET/radical addition/cyclization/SET/deprotonation processes.

Language: Английский

Citations

0
Cascade hydroarylation/Diels–Alder cycloaddition of alkynylindoles with electron-deficient alkynes and alkenes DOI

Guang-Chao Feng,

Jun-Chi Li,

Huang Xiang

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 60(3), P. 328 - 331

Published: Dec. 4, 2023

Herein, a novel cascade gold(I)-catalyzed hydroarylation of alkynylindoles and subsequent Diels-Alder cycloaddition with electron-deficient alkynes alkenes is described. A variety azepino-fused hydrocarbazoles carbazoles were obtained in moderate to excellent yields. Key features this methodology are low catalyst loadings, high regioselectivity, broad functional group tolerances, access important heterocycles, 100% atom economy.

Language: Английский

Citations

4
FeCl3-catalyzed AB2 three-component [3 + 3] annulation: an efficient access to functionalized indolo[3,2-b]carbazoles DOI

Gowsia Jan,

Diksha Rajput,

Anish Gupta

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(23), P. 5978 - 5985

Published: Jan. 1, 2023

An FeCl 3 -catalyzed AB 2 three-component reaction of indole-2-carbaldehydes and 5-aminopyrazoles was established for the synthesis indolo[3,2- b ]carbazoles.

Language: Английский

Citations

3
Palladium Catalysis: Dependence of the Efficiency of C−C Bond Formation on Carboxylate Ligand and Alkali Metal Carboxylate or Carboxylic Acid Additive. Part C: The Domino Diarylation and Annelation Reactions DOI Open Access
Jacques Мuzart

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(22), P. 3784 - 3813

Published: Oct. 3, 2023

Abstract The efficiency of the formation C−C bonds under palladium catalysis often depends on nature carboxylate ligand and carboxylic acids or alkali metal carboxylates additives. This review which is Part C a trilogy devoted to topic, highlights influence units domino diarylation annelation reactions. plausible reaction mechanisms are presented with, as far possible, personal comments.

Language: Английский

Citations

2
Development of 3-triazenylaryne and its application to iterative aryne reactions via o-triazenylarylboronic acids DOI
Motoki Ito,

Yuta Takishima,

Rinto Ishikawa

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(96), P. 14249 - 14252

Published: Jan. 1, 2023

A novel aryne species 3-triazenylaryne has been developed as a divergent platform for the generation of 3-alkynylaryne through o -triazenylarylboronic acids.

Language: Английский

Citations

2
Access to Piperazine-Fused Pyrrolocarbazoles Enabled by Acid-Catalyzed Stereoselective Hydroarylation of Ynamide–Indoles and Subsequent Diels–Alder Reactions/Aromatizations DOI

Ze Zhou,

Xiang Huang,

Qingyi Wei

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7273 - 7278

Published: Aug. 12, 2024

Pyrrolocarbazole skeletons are well known to possess a variety of biological activities that might be therapeutically useful in the treatment cancers. Herein, an acid-catalyzed stereoselective hydroarylation/Diels–Alder cycloaddition/aromatization ynamide–indoles is described. We newly designed and synthesized piperazine-fused pyrrolocarbazole derivatives could further applied synthesis potent Wee1 inhibitors.

Language: Английский

Citations

0
Five-membered ring systems: Pyrroles and benzo analogs DOI
Chuan Shan, Justin M. Lopchuk

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 123 - 173

Published: Jan. 1, 2024

Language: Английский

Citations

0