Design, synthesis, crystal structure and DFT analysis of (E)-N-(tert-butyl)-11H-benzo[4,5]imidazo[2,1-a]isoindol-11-imines with dual-state emission property DOI
Siyu Hou, Xu Wang, Jinping Fu

et al.

Journal of Molecular Structure, Journal Year: 2023, Volume and Issue: 1299, P. 137217 - 137217

Published: Dec. 1, 2023

Language: Английский

Synthesis of Bis-Heterocycles Bearing Methyleneindole Motifs by Pd-Catalyzed Domino Reaction DOI
Lei Wang, Ruixin Chen,

Shuaijie Wu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1941 - 1955

Published: Jan. 23, 2024

A highly robust, general, and practically simple palladium-catalyzed domino bicyclization strategy is presented to synthesize nitrogen-containing bis-heterocycles bearing methylene indole motifs from alkyne-tethered carbamoyl chlorides β,γ- or γ,δ-unsaturated hydrazones. The salient features of this transformation include broad substrate scope, good functional group tolerance, ease for scale-up, convenient conversion.

Language: Английский

Citations

2
Accessing Furan-Linked Methylene Oxindoles/Benzofurans via Stereoselective Palladium-Catalyzed Domino Cyclization/Cycloisomerization DOI

Yujie Yi,

Ye Yuan, Songsong Zhu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12085 - 12093

Published: Aug. 24, 2024

A palladium-catalyzed domino cyclization/cycloisomerization reaction of alkyne-tethered carbamoyl chlorides with (E)-β-chloroenones is reported. This proceeds via a syn-carbopalladation the alkyne, followed by vinyl-PdII-catalyzed cycloisomerization (E)-β-chloroenone cascade, which provides an efficient method to synthesize furan-linked methylene oxindoles. The features stereodefined vinyl-PdII species, high excellent 5-exo/6-endo selectivity, Z/E and sequential formation three bonds bis-heterocycles. strategy for synthesis furan-containing benzofurans has also been demonstrated.

Language: Английский

Citations

2
Experimental and computational studies on the palladium-catalyzed intramolecular dearomatization, electrophilic addition, intermolecular coupling sequence DOI
Qinghui Liu, Yue Ma, Hong‐Yu Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(5), P. 1357 - 1365

Published: Dec. 28, 2023

An unprecedented Pd-catalyzed highly stereoselective synthetic strategy for the construction of a broad spectrum polycyclic fused indoline skeletons employing N -halobenzoyl o -haloanilines and -(prop-2-yn-1-yl)anilines as has been described.

Language: Английский

Citations

4
Advances in Cyclizative Dimerization of Alkynes and Allenes for the Complex Bis-heterocyclic Compounds Synthesis DOI

Luning Tang,

Maoyan Liao,

Biao Zhu

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 163, P. 134158 - 134158

Published: July 20, 2024

Language: Английский

Citations

1
DFT-Assisted Atroposelective Construction of Indole-Fused N-Heteroaromatic Frameworks through Palladium-Catalyzed C–H Imidoylation DOI
Xilong Wang, Jiali Xu, Yu Luo

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 15(1), P. 201 - 210

Published: Dec. 16, 2024

On the basis of density functional theory (DFT) calculations, we designed an asymmetric synthesis method for axially chiral biaryls through C(sp2)–H imidoylative cyclization isocyanides. Building on this, successfully synthesized compounds containing indole-fused N-heteroaromatic frameworks via palladium-catalyzed C–H imidoylation to achieve high yields and enantioselectivity. Various efficient pathways facilitated ring derivatives with either C–C or C–N axial chirality. This not only provides diverse strategy but also demonstrates that DFT-assisted design is a reliable tool accurately predicting reaction stereoselectivity effectively reducing workload chemical experiments.

Language: Английский

Citations

1
A Highly Selective Synthesis of (E)‐11‐Arylidenebenzo [4′,5′] thieno [2′,3′ : 4,5] Pyrimido [2,1‐a] Isoindol‐13(1H)‐ones via Copper‐Catalyzed Sonogashira Coupling and Hydroamination DOI
Heng He,

Zhen-Xu Wang,

Meimei Zhang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(8)

Published: May 24, 2024

Abstract An efficient and highly selective reaction of 2‐(2‐bromophenyl)‐5,6,7,8‐tetrahydrobenzo [4,5] thieno[2,3‐ d ]pyrimidin‐4(3 H )‐one terminal alkyne has been developed under palladium‐free conditions by CuI‐catalyzed sequential Sonogashira coupling 5‐exo‐dig hydroamination reaction. A series 11‐arylidene‐2,3,4,11‐tetrahydrobenzo [4′,5′]thieno [2′,3′ : 4,5]pyrimido [2,1‐ a ]isoindol‐13(1 derivatives with only the (E) ‐configuration were obtained.

Language: Английский

Citations

0
Palladium-Catalyzed Domino Carboetherification Reactions: Synthesis of Bis-Heterocycles Bearing Isoxazoline and Methyleneindole Motifs DOI

Feifei Jin,

Qing Wu,

Shuaijie Wu

et al.

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

Published: Dec. 18, 2024

A novel and highly efficient Pd-catalyzed approach for the synthesis of bis-heterocycles featuring both isoxazoline methyleneindole motifs is demonstrated. The in situ formation vinyl Pd(II) species through an alkyne-tethered carbamoyl chloride cyclization crucial, innovative carboetherification β,γ-unsaturated oximes with has been developed. This method not only operationally straightforward but also exhibits a broad substrate scope excellent functional group tolerance.

Language: Английский

Citations

0
Design, synthesis, crystal structure and DFT analysis of (E)-N-(tert-butyl)-11H-benzo[4,5]imidazo[2,1-a]isoindol-11-imines with dual-state emission property DOI
Siyu Hou, Xu Wang, Jinping Fu

et al.

Journal of Molecular Structure, Journal Year: 2023, Volume and Issue: 1299, P. 137217 - 137217

Published: Dec. 1, 2023

Language: Английский

Citations

0