Base-promoted [4 + 2] annulation of pyrrole-2-carbaldehyde derivatives with β,γ-unsaturated α-ketoesters: syntheses of 5,6-dihydroindolizines DOI

You‐Ya Zhang,

Lin Li, Ai‐Jun Ma

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(44), P. 8633 - 8637

Published: Jan. 1, 2022

A base-promoted [4 + 2] annulation of pyrrole-2-carbaldehyde derivatives with β,γ-unsaturated α-ketoesters for the syntheses multisubstituted 5,6-dihydroindolizines was developed.

Language: Английский

Multiple-fold C–F bond functionalization for the synthesis of (hetero)cyclic compounds: fluorine as a detachable chemical handle DOI
Danhua Ge, Xue‐Qiang Chu

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(7), P. 2013 - 2055

Published: Jan. 1, 2022

We highlighted the recent advances in field of multiple-fold C–F bond functionalization for synthesis (hetero)cyclic compounds.

Language: Английский

Citations

48
Single-atom skeletal editing of 2H-indazoles enabled by difluorocarbene DOI
Yao Zhou,

F Chen,

Ziru Li

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(7), P. 1975 - 1981

Published: May 11, 2023

Language: Английский

Citations

29
Mechanochemical Synthesis of 1,2-Diketoindolizine Derivatives from Indolizines and Epoxides Using Piezoelectric Materials DOI
Yumei Wang,

Ziwu Zhang,

Lichan Deng

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(18), P. 7171 - 7176

Published: Aug. 30, 2021

A simple and efficient mechanochemical-induced approach for the synthesis of 1,2-diketoindolizine derivatives has been developed. BaTiO3 was used as piezoelectric material in this transformation. This method features no usage solvent, experimental operation, scalable potential, high conversion efficiency, which make it attractive practical.

Language: Английский

Citations

55
B2pin2-Mediated Cascade Cyclization/Aromatization Reaction: Facial Access to Functionalized Indolizines DOI
Xiaoning Li,

Zunsheng Chen,

Weiming Chen

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(40), P. 7372 - 7377

Published: Sept. 29, 2022

Herein, a B2pin2-mediated radical cascade cyclization/aromatization reaction of enaminone with pyridine is described. This strategy provides practical way for the construction valuable functionalized indolizines under metal-, external oxidant-, and base-free conditions, which could be compatible various kinds functional groups, such as halogen, π-system, heterocycle, ferrocenyl, etc. A preliminary mechanism investigation indicated that pyridine-boryl formed in situ triggered to occur.

Language: Английский

Citations

31
Mechanochemically Induced Dehydrogenation Coupling and [3+2] Cycloaddition of Indolizines with Allenes Using Piezoelectric Materials DOI

Mingzhou Huang,

Lichan Deng,

Tianfeng Lao

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(5), P. 3265 - 3275

Published: Jan. 26, 2022

A wide range of indolizines with allenes proceeded smoothly under mechanochemically induced conditions via a [3+2] annulation process, affording various substituted pyrrolo[2,1,5-cd]indolizines in good yields. The reaction efficiency was greatly improved by using piezoelectric material as the charge transfer catalyst. photophysical properties resulting pyrrolo[2,1,5-cd]indolizine were characterized.

Language: Английский

Citations

27
Metal-free synthesis of gem-difluorinated heterocycles from enaminones and difluorocarbene precursors DOI
Fei Wang, Rui Fu, Jie Chen

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(21), P. 3477 - 3480

Published: Jan. 1, 2022

A cascade strategy to synthesise gem-difluorinated 2H-furans from reactions of BrCF2CO2Et with enaminones has been described. The tolerate a wide variety functional groups under metal-free conditions. An active aminocyclopropane is proposed be key intermediate through the cyclopropanation difluorocarbene enaminones, which further triggers regioselective C-C bond cleavage in situ afford corresponding 2H-furans.

Language: Английский

Citations

24
Synthesis of Indolizines via Tf2O-Mediated Cascade Reaction of Pyridyl-enaminones with Thiophenols/Thioalcohols DOI
Changyuan Zhang, Wei Wang,

Xuncheng Zhu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(7), P. 1192 - 1197

Published: Feb. 13, 2023

A cost-effective, highly regioselective and metal-free version for the synthesis of indolizine derivatives by means Tf2O-mediated cascade reaction pyridyl-enaminones thiophenols/thioalcohols under mild conditions has been reported. Diverse electron-rich could be obtained in up to 94% yield via selective 1,4-addition vinyl iminium triflate tandem cyclization/aromatization, which allowed simultaneous construction C–N C–S/and one example C–Se bonds.

Language: Английский

Citations

15
Base-controlled selective cleavage of the C–F bond of difluorocarbene for the divergent assembly of indolizines DOI
Chun‐Yan Wu, Xiang‐Long Chen, Dongsheng Yang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(15), P. 4214 - 4218

Published: Jan. 1, 2024

A [3 + 1 1] cascade annulation reaction for the divergent construction of trisubstituted indolizines using sulfoxonium ylides, BrCF 2 CO Me and pyridinium salts as readily available substrates has been developed.

Language: Английский

Citations

5
Electro-Oxidative sp3 C–H Bond Functionalization and Annulation Cascade: Synthesis of Novel Heterocyclic Substituted Indolizines DOI

Bhanwar Kumar Malviya,

Amanpreet Kaur Jassal, Manvika Karnatak

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(5), P. 2898 - 2911

Published: Feb. 1, 2022

Indolizine derivatives are prevalent in many synthetic intermediates, pharmaceuticals, and organic materials. Herein, we report a novel electro-oxidative cascade cyclization reaction that uses electricity as the primary energy input to promote reaction, leading series of heterocyclic substituted indolizine under exogenous-oxidant-free conditions. It is noteworthy this electrochemical method provides strategy for generating diversity quinazolinones quinolines on indolizines. In addition, sole byproduct was molecular hydrogen.

Language: Английский

Citations

20
Copper-Catalyzed Formal [4 + 1] Annulation toward Diverse Trifunctionalized Indolizines from Pyridinium 1,4-Zwitterionic Thiolates and Diazos DOI
Wen Li, Hexiang Wang, Yuan Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7199 - 7207

Published: May 12, 2023

Pyridinium 1,4-zwitterionic thiolates were regarded as powerful and versatile building blocks to prepare nitrogen- sulfur-containing heterocycles. Herein, we reported a copper-catalyzed formal [4 + 1] annulation of pyridinium diazo compounds without any additives access library trifunctionalized indolizines in good yields. Besides, isoquinolinium imidazolium also applied this reaction. Of particular note is that various functional groups such -CO2R, -CO2NR2, -CF3, -CN, -(O)P(OR)2 could be easily introduced into cycloaddition products by strategy.

Language: Английский

Citations

11