An Environmentally Benign Radical Annulation of Α,Β-Unsaturated Ketoxime Acetates with 3-Formylchromones for the Synthesis of Functionalized 2,4-Diarylpyridines DOI
Sheng‐Jiao Yan, Jing Yang,

Xing-Mei Hu

et al.

Published: Jan. 1, 2023

A novel synthesis method has been developed for the construction of functionalized 2,4-diarylpyridines. The reaction involves several key processes, including a radical Michael occurring twice, two SET mechanisms, proton loss, aldehyde oxidation, decarboxylation, and ring-opening reaction. All these processes are facilitated by refluxing mixture starting materials in environmentally benign solvent, propylene carbonate (PC), with oxidant (air) catalyst Cu(OAc)2. This cascade not only forms new bonds but also cleaves three existing single pot. protocol presented this study is valuable tool synthesizing unsymmetrical

Language: Английский

Synthesis of medium-sized benzo[b]azocines and benzo[b]azonines by photoinduced 8-/9-endo sulfonyl-cyclization DOI
Kai Sun, Dongyang Zhao, Quanxin Li

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(8), P. 2309 - 2316

Published: July 24, 2023

Language: Английский

Citations

40

Concise synthesis of pyrrolo[3,4-c]quinolines via a P(NMe2)3-catalyzed [4 + 2] annulation followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization DOI
Zhengyang Chen, Dan Xiong, Nengzhong Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(10), P. 2762 - 2767

Published: Jan. 1, 2024

A P(NMe2)3-catalyzed [4 + 2] annulation of 2-amino-β-nitrostyrenes and β′-acetoxy allenoates followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization has been developed.

Language: Английский

Citations

9

Copper-Catalyzed Annulation of O-Acyl Oximes with Cyclic 1,3-Diones for the Synthesis of 7,8-Dihydroindolizin-5(6H)-ones and Cyclohexanone-Fused Furans DOI
Hai‐Tao Yang,

Su-Qing Zhou,

Danmei Chen

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(5), P. 838 - 842

Published: Jan. 27, 2023

A copper-catalyzed annulation of O-acyl oximes with cyclic 1,3-diones has been developed for the concise synthesis 7,8-dihydroindolizin-5(6H)-ones and cyclohexanone-fused furans through substituent-controlled selective radical coupling process. 2-Alkyl undergo C-C coupling, while 2-unsubstituted C-O coupling.

Language: Английский

Citations

18

Base-Mediated Cascade Lactonization/1,3-Dipolar Cycloaddition Pathway for the One-Pot Assembly of Coumarin-Functionalized Pyrrolo[2,1-a]isoquinolines DOI
Qiang Tang, Yanan Liu,

Binbin Fei

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8420 - 8434

Published: June 5, 2024

An elegant and highly concise strategy for the construction of coumarin-functionalized pyrrolo[2,1-a]isoquinolines from available propargylamines isoquinolinium N-ylides has been disclosed. In this reaction, acted as a C2 synthon to form coumarin ring well 1,3-dipole construct pyrrole in single pot. This cascade process involves 1,4-conjugate addition/lactonization/1,3-dipolar cycloaddition four chemical bonds (one C–O bond three C–C bonds) two new heterocyclic skeletons. Additionally, most these compounds showed good fluorescence properties exhibited high molar extinction coefficient large Stokes shifts.

Language: Английский

Citations

6

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

Controllable stepwise fluorine elimination strategy for the chemodivergent synthesis of pyrido[2,1-a]isoquinolines DOI Creative Commons

Qiuyun Li,

Zili Liu,

R. F. Li

et al.

Green Synthesis and Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: March 1, 2025

Language: Английский

Citations

0

Copper-Catalyzed [3 + 2] Annulation of O-Acyl Oximes with 4-Sulfonamidophenols for the Synthesis of 5-Sulfonamidoindoles and 2-Amido-5-sulfonamidobenzofuran-3(2H)-ones DOI

Zi-Jun Hu,

Wei Chen,

Xinyu Lyu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4229 - 4234

Published: May 13, 2024

A copper-catalyzed [3 + 2] annulation of

Language: Английский

Citations

3

(3+2) Cycloaddition of Heteroaromatic N-Ylides with Sulfenes DOI
Kosuke Yamamoto,

Kohei Torigoe,

Masami Kuriyama

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(4), P. 798 - 803

Published: Jan. 22, 2024

A (3+2) cycloaddition of heteroaromatic N-ylides with sulfenes, which are generated in situ from sulfonyl chlorides, has been developed. variety ylides were transformed into the corresponding sulfone-embedded N-fused heterocycles high yields. Hexafluoroisopropyl mesylate was demonstrated to be a suitable reactant for quinolinium ylides. Furthermore, this could performed an ylide prepared by Cu-catalyzed transfer reaction one-pot manner, extending substrate scope unisolable ylide.

Language: Английский

Citations

2

Copper-catalyzed [3+2] annulation of O-acyl ketoximes with 2-aryl malonates for the synthesis of 3-aryl-4-pyrrolin-2-ones DOI

Xiaoqing Song,

Xiao-Qi Qiang,

Zi-Jun Hu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(35), P. 5225 - 5228

Published: Jan. 1, 2023

A copper-catalyzed [3+2] annulation of O -acyl ketoximes with 2-aryl malonates for the concise synthesis 3-aryl-4-pyrrolin-2-ones has been developed.

Language: Английский

Citations

5

Photoinduced sulfonylation cyclization to medium-sized benzo[b]azocine and mechanistic insight DOI
Dongyang Zhao, Kai Sun, Miao Tian

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(13), P. 3313 - 3320

Published: Jan. 1, 2023

A novel light induced 8-endo sulfonyl cyclization to medium-sized benzo[ b ]azocines is developed. DFT calculations rationalize the rate-determining step and chemoselectivity observed in this transformation.

Language: Английский

Citations

5