Cu-TEMPO catalyzed synthesis of benzo[a]acridines and their photophysical studies DOI

Nagarajan Sambavi,

Fazlur‐Rahman Nawaz Khan

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: unknown, P. 155446 - 155446

Published: Dec. 1, 2024

Language: Английский

Synthesis of Heptacyclic Compounds through C–H Bond Activation-Initiated Cascade Reactions DOI
Xing He,

Kangli Liu,

Shengnan Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7425 - 7430

Published: Aug. 22, 2024

Presented herein is an atom- and step-economical method enabling the precise assembly of a heptacyclic scaffold containing both azocine indoline units through cascade reactions indolin-1-yl(aryl)methanimines with diazo indanediones. The formation products involves C–H bond activation double carbene insertion followed by intramolecular condensation, retro-[2 + 2] cycloaddition, recyclization. This reaction not only provided concise straightforward strategy for synthesis otherwise difficult to obtain compounds from readily available substrates but also disclosed unprecedented mode derivatives compounds. In general, this novel synthetic protocol has advantages, such as easily obtainable substrates, structurally sophisticated products, procedure, good compatibility diverse functional groups, ready scalability. Moreover, thus obtained showed decent antiproliferative activity against three human cancer cell lines.

Language: Английский

Citations

8
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

5
Synthesis of CF3-Azafluorenes through the Cascade Reaction of 2H-Imidazoles with CF3-Ynones DOI
Hao Li,

Shengnan Yan,

Chunhua Ma

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 25, 2024

A concise synthesis of trifluoromethyl (CF

Language: Английский

Citations

5
Synthesis of C2-Spiroindolines Based on the Cascade Reaction of 2-Aryl-3H-indoles with Cyclopropanols DOI

Xueying Yang,

Yuanshuang Xu, Xinying Zhang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 694 - 694

Published: Jan. 1, 2025

Language: Английский

Citations

0
Ring-Opening Cyclization (ROC) of spiro-Epoxyoxindoles with Indoles/Aldehydes: An Easy Access to Polyheterocyclic spiro-Oxindoles DOI

Bharat Singh,

Suraj Kashyap,

Hitesh K. Soni

et al.

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

Published: March 10, 2025

A simple one-pot, two-step strategy for the synthesis of three-dimensional (3D) polyheterocyclic spiro-oxindoles by Lewis-acid-catalyzed Friedel–Crafts type C-3 alkylation indoles via regioselective nucleophilic ring opening spiro-epoxyoxindoles, followed p-TSA-catalyzed Pictet-Spengler reaction with aldehydes in up to 98% yield and 1.4:1 diastereomeric ratio has been developed.

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
Photochemical Functionalization of 4-Diazoisoquinoline-1,3(2H,4H)-diones and Their 1-Sulfoxide Analogues DOI Creative Commons
Joseph P. Milton, Dorota Gryko

ACS Organic & Inorganic Au, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

Language: Английский

Citations

0
Photoredox-Catalyzed Carbamoyl Radical-Initiated Dearomative Spirocyclization To Access Spiro-Cyclohexadiene Oxindoles DOI
Chunhua Ma, Qing Guo,

Hui Meng

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(40), P. 8503 - 8508

Published: Oct. 1, 2024

The sustainable construction of spirocyclic compounds is important to the scientific community and pharmaceutical industries. Herein, we demonstrate a carbamoyl radical-initiated intramolecular dearomative spirocyclization access spiro-cyclohexadiene oxindoles under visible light irradiation, which constitutes first example accessing I-substituted derivatives that facilitate diversified transformations. Additionally, scalability, late-stage modification drugs, significant antitumor activity products novel synthesis platform for expediting drug development.

Language: Английский

Citations

2
Recent Advances in the Synthetic Applications of Nitrosoarene Chemistry DOI
Feng Lin, Rongzhi Tang, Sheng Liu

et al.

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

Published: Nov. 20, 2024

This review covers reactions involving nitrosoarenes over the last decade, including cyclization, with attacks at oxygen or nitrogen terminus, dimerization, rearrangement, coordination, and other significant reactions.

Language: Английский

Citations

1
Quinazolinone-to-Isoquinoline Metamorphosis by Ruthenium-Catalyzed [4+2] Annulation with Sulfoxonium Ylides DOI
Xiaogang Wang, Fei Yuan, Michal Szostak

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(50), P. 10951 - 10957

Published: Dec. 10, 2024

Molecular editing of quinazolinones to isoquinolines by a novel ruthenium-catalyzed [4+2] annulation with sulfoxonium ylides has been developed. The method permits the precise and rapid assembly multisubstituted aminoisoquinolines, class heterocycles that play privileged role in organic synthesis pharmaceutical development. This new catalytic process exhibits programmability, including directed C–H acetylation, nucleophilic cyclization, alcoholysis. Remarkably, various 2-arylquinazolinones could be employed excellent yields broad functional group tolerance. heterocycle-to-heterocycle protocol is compatible green chemistry using an EtOH solvent releasing H2O dimethyl sulfoxide as byproducts.

Language: Английский

Citations

1