Synthesis of functionalized tetrahydrodibenzo[b,g][1,8]naphthyridin-1(2H)-ones through base-promoted annulation of quinoline-derived dipolarophiles and cyclic enaminones DOI

Wenjun Luo,

Xinghua Zheng,

Fanglian Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(48), P. 9524 - 9529

Published: Jan. 1, 2023

An eco-friendly and metal-free method for the synthesis of tetrahydrodibenzo[b,g][1,8]naphthyridin-1(2H)-ones was established. Quinoline-derived dipolarophiles cyclic enaminones as starting materials undergo a 1,4-Michael addition/SNAr tandem annulation reaction affording target products. This approach features transition conditions, good functional group tolerance operational simplicity.

Language: Английский

Silver‐catalyzed Cascade Bis‐heteroannulation Reaction of Enynones and o‐Hydroxyphenyl Enaminones: Access to Highly Functionalized 3‐Furylmethyl Chromones DOI

Mingshuai Zhang,

Meichen Liu,

Yuetong Qiu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2363 - 2369

Published: March 16, 2024

Abstract A synthetic protocol was developed to synthesize highly functionalized 3‐furylmethyl chromones from enynones and o ‐hydroxyphenyl enaminones via silver‐catalyzed cascade bis‐heteroannulation reaction. This strategy features broad substrate scope good functional group tolerance. Furthermore, the chromone skeleton shows potential application value through further gram‐scale synthesis derivatization.

Language: Английский

Citations

13

Rh-Catalyzed and Self-Directed Aromatic C–H Activation of Enaminones to Divergent Alkenylated and Annulated Compounds DOI

Demao Chen,

Jie‐Ping Wan, Yunyun Liu

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 27, 2025

By means of simple Rh catalysis, the direct activation ortho-C-H bond in aryl enaminones has been realized with enaminone structure as a traceless directing fragment. The products resulting from C-H alkenylation and further annulation via intramolecular addition could be accessed depending upon alkenes. annulated used for easy synthesis valuable 2-aza-fluorenones one-pot operation by employing NH4OAc.

Language: Английский

Citations

2

Catalytic C H activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones DOI

Qiuyun Li,

Yannan Zhu, Yining Wang

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(9), P. 109494 - 109494

Published: Jan. 6, 2024

Language: Английский

Citations

7

Oxidative Free-Radical C(sp2)–H Bond Chlorination of Enaminones with LiCl: Access to Highly Functionalized α-Chlorinated Enaminones DOI

Yunhua Xie,

Zhilai Zhang,

Biao Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(12), P. 8521 - 8530

Published: June 3, 2024

An oxidative free-radical C(sp2)–H bond chlorination strategy of enaminones has been developed by using LiCl as a chlorinating reagent and K2S2O8 an oxidant. This transformation provides new straightforward synthetic methodology to afford highly functionalized α-chlorinated with Z-configuration in good excellent yields.

Language: Английский

Citations

6

Synthesis of 4-Alkylated 1,4-Dihydropyridines: Fe(II)-Mediated Oxidative Cascade Cyclization Reaction of Cyclic Ethers with Enaminones DOI

Yulin Sun,

Zhuoyuan Liu, Donghan Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(16), P. 11627 - 11636

Published: Aug. 9, 2023

Syntheses of highly functionalized 4-alkylated 1,4-dihydropyridines (1,4-DHPs) from cyclic ethers and enaminones via iron(II)-mediated oxidative free radical cascade C(sp3)-H bond functionalization/C(sp3)-O cleavage/cyclization reaction have been first developed. This novel synthetic strategy offers an alternative method for the construction 1,4-DHPs by using esters as C4 sources, well expands application in heterocycle synthesis.

Language: Английский

Citations

10

Copper(II)‐Catalyzed [2+2+2] Annulation of Enaminones with Maleimides Using a Traceless Directing Group Strategy DOI
Leiqing Fu, Hongxiang Huang, Yingying Jiang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(19), P. 4139 - 4144

Published: July 2, 2024

Abstract A copper‐catalyzed annulation of enaminones with maleimides was developed to synthesize various pyrrolo[3,4‐e]isoindoles. In this strategy, 2‐aminopyridine served as a traceless directing group, and target products were obtained in 54–72% yields. Moreover, plausible mechanism for reaction proposed based on several control experiments, deuterium exchange previous reports.

Language: Английский

Citations

3

Tandem Synthesis of Polysubstituted Pyrroles via Cu(I)-Catalyzed Cyclization of Ketene N,S-Acetals with β-Ketodinitriles DOI
Anup Sharma,

Mahesh Kumar,

Shiv Chand

et al.

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

Published: March 11, 2025

A new approach to multifunctionalized pyrroles has been explored by the tandem cyclization of α-oxoketene-N,S-acetals with β-ketodinitriles using Cu(MeCN)4BF4 and Ag2CO3 in toluene under reflux conditions. The reaction involves C–C/C–N bond creation, is assumed proceed via enamine formation, intramolecular cyclization, rearrangement. potential methodology also demonstrated for a gram-scale as well some useful organic transformations. offers practical pathway achieve polysubstituted broad substrate scope good functional group tolerance.

Language: Английский

Citations

0

Cu(II)‐Catalyzed Annulation of o‐Phenylenediamines and Phenacyl Bromides for the Facile Synthesis of 2‐Functionalized Quinoxalines DOI
Yongchao Wang, Yu Chen,

Z. XIONG

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(18)

Published: May 1, 2025

Abstract A facile Cu(II)‐catalyzed annulation of o ‐phenylenediamine and phenacyl bromides in EtOH has been developed. In this protocol, diverse 2‐functionalized quinoxalines were prepared 74%–91% yields with high chemoselectivity. The salient features are the excellent yields, broad substrate scope, mild reaction conditions, large‐scale preparation. This not only fills gap conventional metal‐catalyzed o‐phenylenediamine but also provides a practical strategy for construction quinoxalines.

Language: Английский

Citations

0

Construction of 1,4-Dihydropyridines: The Evolution of C4 Source DOI
Siyu Song, Yongchao Wang, Fuchao Yu

et al.

Topics in Current Chemistry, Journal Year: 2023, Volume and Issue: 381(5)

Published: Sept. 25, 2023

Language: Английский

Citations

7

Divergent Synthesis of Enynals and Dihydrobenzo[f]isoquinolines via Deoxyalkynylation of Enaminones Enabled by the Cooperative Action of Tf2O/Pd/Cu DOI
Jianping Lin,

Jiakai Tian,

Lu Yu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16419 - 16425

Published: Oct. 28, 2024

A variety of enynals and dihydrobenzo[

Language: Английский

Citations

2