Recent Advances for the Transformation of Maleimides via Annulation DOI
Mohammad Aslam, Muhammad Saeed Akhtar, Hee Nam Lim

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

This review highlights recent advances in maleimide-based annulation and cyclization strategies, offering insights into their synthetic versatility potential applications creating structurally diverse aromatics bioactive heterocycles.

Language: Английский

Synthesis of Indenone-Fused Pyran Derivatives from Aryl Enaminones and Cyclopropenones through Unsymmetrical Relay C–H Bond Activation and Double C–C/C–O Bond Formation DOI

Chun Xia Yang,

Bin Li, Xinying Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6602 - 6607

Published: July 30, 2024

Presented herein is a novel synthesis of indenone-fused pyran derivatives via the cascade reactions aryl enaminones with cyclopropenones. The formation products involves one-pot procedure consisting C–H bond and enamine functionalization along C–C cleavage cyclopropenone 1,3-rearrangement in situ-formed allylic alcohol moiety followed by intramolecular O-nucleophilic addition Me2NH elimination. To our knowledge, this first simultaneous both indenone scaffolds through concurrent unsymmetrical relay activation double C–C/C–O formation. Moreover, usefulness method further showcased its suitability for large-scale synthetic scenarios diverse transformations products.

Language: Английский

Citations

6
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

0
Synthesis of Benzoisochromene Derivatives via C–H Activation-Initiated Cascade Formal [4+2] and [2+4] Annulation of Aryl Enaminone with Vinyl-1,3-dioxolan-2-one DOI

Chun Xia Yang,

Bin Li, Peng Shi

et al.

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

Published: March 19, 2025

Cascade annulation reactions can assemble structurally intricate polycyclic molecules from simple starting materials with enhanced efficiency and minimized production of waste. Presented herein is a concise effective synthesis benzoisochromene derivatives based on C-H activation-initiated cascade formal [4+2]/[2+4] aryl enaminone vinyl-1,3-dioxolan-2-one. In constructing the six-membered carbocycle, acted as C4 synthon while vinyl-1,3-dioxolan-2-one C2 synthon. O-heterocycle, other hand, former latter C3O1 To our knowledge, this first simultaneous construction both carbocycle an O-heterocycle via concurrent C-H/C-N/C-O bond cleavage C-C/C-C/C-O formation. general, novel protocol features use readily obtainable substrates broad scope, excellent atom- step-economy, intriguing reaction pathway, valuable products.

Language: Английский

Citations

0
Recent Advances in Site Selective Transformations of β-Enaminones via C-H Functionalization/Annulation DOI
Prasanta Ray Bagdi, Karuna Mahato,

Divya Shrestha

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

β-Enaminone transformation strategies are widely employed in the synthesis of numerous biologically active drugs and natural products, highlighting their significance medicinal chemistry.

Language: Английский

Citations

3
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
Ruthenium(II)-Catalyzed Annulation of Oximes with Maleimides: Synthesis of Pyrrolo[3,4-c]isoquinoline-1,3-diones DOI
Ebrahim Kianmehr, Maryam Shafiee-Pour

Organic Letters, Journal Year: 2024, Volume and Issue: 26(33), P. 6977 - 6982

Published: Aug. 5, 2024

A series of pyrroloisoquinoline-1,3-diones has been synthesized using ruthenium(II) as the catalyst and oxygen oxidant in a straightforward manner. The reaction proceeds through tandem C-C/C-N bond formation process between maleimides ketoximes, providing direct approach for synthesis titled products. This operationally simple procedure supplies suitable conditions synthesizing diverse isoquinoline-based heterocycles with range functional groups moderate to good yields compatible gram-scale synthesis. Furthermore, compatibility this green environmentally friendly raises importance present method.

Language: Английский

Citations

1
One‐Pot Synthesis of 3‐Hydroxy‐1H‐Pyrrolo[3,4‐b]quinolin‐1‐one via Enaminamides DOI

Xi Shen,

Zhi‐Cheng Yu,

You Zhou

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(21), P. 4399 - 4403

Published: July 16, 2024

Abstract A multicomponent cascade cyclization reaction using aryl methyl ketones, amines, and enaminamide reagents to construct 3‐hydroxy‐1 H ‐pyrrolo[3,4‐ b ]quinolin‐1‐one skeleton with good substrate compatibility (50 examples) has been reported. The one‐pot, metal‐free process formed two C−C bonds, C−N a tetrasubstituted carbon stereocenter containing hydroxyl group. enabled modified transformation of drug molecules derivatization products.

Language: Английский

Citations

0
Multicomponent synthesis of functionalized pyrrolo[3,4-e]isoindole-1,3,6,8-tetraones via [2 + 2 + 2] cycloaddition of maleimides with nitroenamines DOI

Jia-Ming Yang,

Bi-Na Shao,

Xing-Mei Hu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(21), P. 6144 - 6149

Published: Jan. 1, 2024

We developed a protocol for the synthesis of PIITOs from maleimides and nitroenamines. This strategy featured [2 + 2 2] cycloaddition with heating mixture substrates 1 DMF without any catalyst.

Language: Английский

Citations

0
Regioselective Oxidation of Tetrahydronaphthalenes to α-Tetralone Derivatives Using DDQ as Oxidizing Agent: Synthesis and Evaluation of Antibacterial and Antifungal Activities DOI Creative Commons

Ahmed Meddeb,

Amal Thebti, Haïtham Elleuch

et al.

ACS Omega, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 11, 2024

An easy and efficient approach for the synthesis of highly regioselective functionalized dihydronaphthalen-1(2

Language: Английский

Citations

0
Controlled Ru (II) & Rh (III) catalyzed [4+2] & [4+1] carbo‐annulation via C–H Activation using Sulfoxonium ylide & Maleimide: Facile access to Fused Benzoisoindole & Spiroindanone DOI

Raju Vaggu,

Akhila Muraharikar,

Y. Prasanna Kumar

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(47)

Published: Sept. 13, 2024

Abstract A well‐ordered strategy of sulfoxonium ylides as a directing group well carbene source for the Ru‐catalysed [4+2] and Rh‐catalysed [4+1] carbo‐annulations with maleimides has been described. These novel methodologies have successfully established synthesis complex spiroindanones benzoisoindoles containing compounds by transition metal‐mediated C−H activation/functionalization reactions. Further, annulated were obtained in absence any oxidant. possible rationale remarkable divergent selectivity between two catalysts proposed.

Language: Английский

Citations

0