Intramolecular/Intermolecular Sequential Cyclization Accompanied by Double C–F Bond Cleavage: Access to Tricyclic Fluorine-Containing Pyrano[3,2-c]chromenes DOI
Dongsheng Yang, Xiang‐Long Chen, Chun‐Yan Wu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16553 - 16563

Published: Oct. 28, 2024

Defluorinative cyclization of CF

Language: Английский

Base-Promoted Regioselective Annulation of Pyridinium Ylides and Bromoalkynes for the Chemodivergent Synthesis of Indolizines DOI

Xiang Wang,

Huayou Hu,

Qiuyun Li

et al.

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

Published: Feb. 5, 2025

A base-promoted regioselective formal [3 + 2] annulation of pyridinium ylides with bromoalkynes is reported, producing a series substituent-diverse indolizines in generally good yields. mild K2CO3-promoted three-component cyclization and at 2:1 molar ratio delivered C2-acylmethylated indolizines, whereas C2-brominated were generated starting from bearing strong electron-withdrawing groups the unit by using 2,2,6,6-tetramethyl-1-piperidinyloxy as dehydrogenating reagent. The current synthetic methodology offers controllable modular approach to access different substitution patterns, featuring wide substrate scope, functional group compatibility, complete regioselectivity without demand any transition-metal catalysts.

Language: Английский

Citations

1

Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts DOI
Farhad Golmohammadi, Chiman Osmani,

Frank Röminger

et al.

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

Published: April 19, 2025

A straightforward and efficient strategy for the synthesis of fully functionalized indolizines has been developed through a transition metal- oxidant-free [3 + 2] cycloaddition reaction zwitterionic ketenimines pyridinium salts. This versatile method proceeds under mild conditions, affording in moderate to good yields. approach involves an intermolecular cycloaddition, followed by enamine/imine tautomerization aromatization. Notably, this demonstrates broad functional group compatibility allows facile scalability, making it valuable tool indolizine-based frameworks organic medicinal chemistry.

Language: Английский

Citations

0

Difluorocarbene-Enabled Trifluoromethylation and Cyclization for the Synthesis of 3-(Trifluoromethyl)-4H-pyrans DOI
Chun‐Yan Wu, Xiang‐Long Chen, Dongsheng Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 27, 2024

A three-component annulation reaction and trifluoromethylation for the construction of 3-(trifluoromethyl)-4

Language: Английский

Citations

2

Recent Advances in the Development of Indolizine Scaffolds: Synthetic Methodology and Mechanistic Insights DOI
Jiuzhong Huang, Chunsheng Li, Xiaoning Li

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 20, 2024

Comprehensive Summary Indolizine is a nitrogen‐containing heterocycle with strong aromaticity, possessing delocalized 10π‐electron system. Based on the indolizine scaffolds, numerous molecules biological activity and organic functional materials have been synthesized. Since 2016, over 110 papers published synthesis of but reviews synthesizing scaffolds incomplete not up‐to‐date. Herein, from perspective structure combination pyrrole pyridine ring, we focus construction through diversity starting substrates, including derivatives (N1‐substituted pyridinium salt derivatives, C2‐substituted N1‐ C2‐free substituted derivatives), unoriginal ring substrates. Furthermore, corresponding reaction mechanisms synthetic methodologies are also elaborated. Therefore, this review only paves way for provides insight into exploring new modes constructing heterocycles. Key Scientists was discovered by Angeli in 1890 first prepared Scholtz 1912 α‐picoline acetic anhydride. A general approach developed Chichibabin 1927, that practical value preparation 2‐alkyl‐ or 2‐arylindolizines. The closure quaternary halides. At begining 21st century, Basavaiah introduced dimension Baylis‐Hillman chemistry leading to novel facile convenient methodology one‐pot operation. In 2010, Barluenga reported Cu(I)‐catalyzed regioselective [3+2] cyclization unsubstituted pyridines toward alkenyldiazoacetates functionalized successful example metal‐catalyzed π‐deficient heterocyclic system alkenyldiazo compounds. 2019 2022, Xi Liu exploited methods non‐pyridine as synthesize indolizines, respectively. Guo an environmentally benign electrooxidative formyl‐ acyl‐substituted indolizines.

Language: Английский

Citations

1

Intramolecular/Intermolecular Sequential Cyclization Accompanied by Double C–F Bond Cleavage: Access to Tricyclic Fluorine-Containing Pyrano[3,2-c]chromenes DOI
Dongsheng Yang, Xiang‐Long Chen, Chun‐Yan Wu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16553 - 16563

Published: Oct. 28, 2024

Defluorinative cyclization of CF

Language: Английский

Citations

0