Regioselective alkenylation of masked carboxylic acid derivatives of coumarins with acrylates via oxidative C(sp2)–C(sp2) cross-coupling DOI

Kalakonda Raga Chaitanya,

Srinivas Ambala,

Bheeshma Geetanjali Kodiripaka

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(47), P. 19742 - 19745

Published: Jan. 1, 2024

Regio-selective C–H alkenylation reaction with acrylates by a rhodium-catalyzed of PMS (phenylmethyl sulfoximine) directed 2-oxo-2 H -chromene-3-carboxylic acid derivatives.

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

Electrocatalytic C–H/S–H Coupling of Amino Pyrazoles and Thiophenols: Synthesis of Amino Pyrazole Thioether Derivatives DOI
Wenbao Zhang, Q. Zou, Qian Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(8), P. 5434 - 5441

Published: April 6, 2024

A mild method for the C–H/S–H coupling of pyrazol-5-amines and thiophenols was developed via electrochemistry, giving diverse amino pyrazole thioether derivatives in 37–98% yields. This electrochemical reaction is sustainable an atom-efficient approach with good functional group tolerance scalability by avoiding metal external chemical oxidants.

Language: Английский

Citations

4

Rh(iii)-catalyzed C(sp2)–H functionalization/[4+2] annulation of oxadiazolones with iodonium ylides to access diverse fused-isoquinolines and fused-pyridines DOI

Wang-Liang Chen,

Jia‐Lin Song,

Sheng Fang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(51), P. 6560 - 6563

Published: Jan. 1, 2024

A Rh( iii )-catalyzed C–H/N–H [4+2] annulation of oxadiazolones with iodonium ylides was developed, which afforded a series fused-isoquinolines and fused-pyridines.

Language: Английский

Citations

4

Switchable Skeletal Rearrangement of Hexahydro-4H-indol-4-ones: Divergent Synthesis of Dihydroxy-4H-cyclopenta[b]pyridin-4-ones and 8-Alkenyl Oxepane-2,6-diones DOI

Zhilai Zhang,

Haifeng Sun,

Mingshuai Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4205 - 4211

Published: May 14, 2024

An unprecedented base-controlled selective skeletal rearrangement reaction of hexahydro-4

Language: Английский

Citations

3

Rh(III)-Catalyzed Redox-Neutral C–H Activation/Annulation of Oxadiazolones with Sulfoxonium Ylides to access oxadiazoloisoquinolinone DOI

Pothapragada S. K. Prabhakar Ganesh,

Eswaran Kamaraj,

Vairaperumal Veeramani

et al.

New Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Oxadiazolone-fused isoquinolines were synthesized via Rh( iii )-catalyzed [4+2] annulation and C–H activation, followed by acymethylation products with antidiabetic anti-inflammatory potential.

Language: Английский

Citations

0

Divergent [5 + 1] Annulation of o-Aminobenzamides with Vinylene Carbonate as a Multifunctional Reagent DOI
Jiang Nan, Hanqing Zhang, Lanxin Zhu

et al.

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

Published: April 3, 2025

A divergent [5 + 1] cyclization reaction of o-aminobenzamides with vinylene carbonate has been developed, rapidly generating three types cyclic molecules including quinazolinones, 2-methylquinazolinones, and 2,3-dihydroquinazolinones high chemoselectivity. In this discovery, blooms as a multifunctional reagent to participate in cyclization. The potential new finding is further emphasized by assembling the benzothiazole heteroarene via [4 version tolerating bioactive units well.

Language: Английский

Citations

0

Iridium(III)-Catalyzed Cyclization of Oximes with Iodonium Ylides: Synthesis of Multisubstituted Heterocyclic N-Oxides DOI

N. Aravindan,

Masilamani Jeganmohan

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

Published: May 29, 2025

Iridium(III)-catalyzed regioselective cyclization of substituted oximes with iodonium ylides has been described. This methodology offered multisubstituted heterocyclic N-oxides under mild reaction conditions in a redox-neutral manner. The was also compatible vinyl oximes. Additionally, substrate diversification carried out to illustrate the synthetic application protocol. A possible mechanism involving C-H bond activation proposed as well supported by isolation key five-membered iridacycle intermediate.

Language: Английский

Citations

0

Transition-Metal-Catalyzed Directed C–H Bond Functionalization with Iodonium Ylides: A Review of the Last 5 Years DOI Creative Commons

Juting Liao,

Dulin Kong, Xiaoyang Gao

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(15), P. 3567 - 3567

Published: July 29, 2024

Transition-metal-catalyzed directed C-H functionalization with various carbene precursors has been widely employed for constructing a wide range of complex and diverse active molecules through metal migratory insertion processes. Among precursors, iodonium ylides serve as novel emerging precursor features including easy accessibility, thermal stability high activity, which have attracted great attention from organic chemists achieved tremendous success in transformation. In this review, recent progress on the application multifunctional coupling characteristics bond activation reactions is summarized, potential discussed.

Language: Английский

Citations

2

Solvent-Controlled Rh(III)-Catalyzed Mono- and Dual Functionalization of Quinolyl Aldoximes with Diazo Compounds DOI
Peng Zhang,

Shan Xu,

Shihaozhi Wang

et al.

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

Published: Nov. 14, 2024

A solvent-controlled Rh(III)-catalyzed mono- and dual-C-H bond activation/carbene migratory insertion with diazo compounds as a single coupling partner was demonstrated. The reaction proceeded under mild conditions, yielding products in good to excellent yields. These results are significant for the development of domino multiple functionalization C(sp

Language: Английский

Citations

2

Redox‐Neutral Nickel‐Catalyzed Selective Hydroalkynylation of Internal Alkyne and Its Application in Anticancer Agent Discovery DOI
Weiming Chen, Teng Liu, Shuqing Li

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 4, 2024

Comprehensive Summary Herein, an unprecedented nickel‐catalyzed regioselective hydroalkynylation of unsymmetrical internal alkynes was realized with steric hindered resistance selectivity via the cyano‐directing group strategy. Significantly, resulting 1,3‐enyne products could be effectively employed in synthesis novel nitrogen‐containing tricyclics compounds, that provided potential candidate compound 8a (IC 50 = 2.6—6.1 μmol/L) for anti‐tumor cell proliferation activity. Therefore, this work not only improves transition‐metal‐ catalyzed strategy alkynes, but also exhibits versatility 1,3‐enynes construction complex bioactive chemical space.

Language: Английский

Citations

1