Iron-catalyzed radical cascade cyclization of oxime esters with isocyanides: synthesis of 1-cyanoalkyl isoquinolines and 6-cyanoalkyl phenanthridines

Xue, Ding; Liu, Rongqi; Zhang, Denggao; Li, Ning; Xue, Yuankun; Ge, Qianwei; Shao, Liming

doi:10.1039/d1ob01556g

Cited by 8 publications

(2 citation statements)

References 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Some pre-functionalized isocyanic substrates are often used to construct various polycyclic nitrogen-containing heterocyclic compounds. Shao’s group achieved facile construction of a series of 1-cyanoalkyl isoquinolines 183 and 6-cyanoalkyl phenanthridines 185 by cyanoalkylation under iron catalysis using various isocyanines ( 184 and 186 ) as substrates and cyclic ketoxime esters 2 as radical precursors ( Scheme 29 ) [ 86 ]. As shown in the proposed mechanism, the radical intermediate 188 has two pathways to obtain the final product: oxidation by Fe 3+ species followed by deprotonation by 1,8-Diazabicyclo [5.4.0]undec-7-ene (DBU) or otherwise direct oxidation by oxime ester 2 after deprotonation.…”

Section: Cyclic Ketoxime Estersmentioning

confidence: 99%

Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters

et al. 2023

View full text Add to dashboard Cite

The synthetic strategies of oxime derivatives participating in radical-type reactions have been rapidly developed in the last few decades. Among them, the N–O bond cleavage of oxime esters leading to formation of nitrogen-centered radicals triggers adjacent C–C bond cleavage to produce carbon-centered free radicals, which has been virtually used in organic synthesis in recent years. Herein, we summarized the radical reactions involving oxime N–O bond and C–C bond cleavage through this special reaction form, including those from acyl oxime ester derivatives and cyclic ketoxime ester derivatives. These contents were systematically classified according to different reaction types. In this review, the free radical reactions involving acyl oxime esters and cyclic ketoxime esters after 2021 were included, with emphasis on the substrate scope and reaction mechanism.

show abstract

Section: Cyclic Ketoxime Estersmentioning

confidence: 99%

Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters

et al. 2023

View full text Add to dashboard Cite

show abstract

“…[30] Selenium-containing compounds have gained the attention of chemists because of their prominence in medicinal chemistry as well as in functionalized organic materials. [31] In 2020, Ji and coworkers [32] reported organoselenyl isoquinolinium imides 17 synthesis by using N'-( 2 Shao and coworkers [33] developed a Fe(II)-catalyzed radical domino cyclization reaction between oxime esters 18 and isocyanides 19 to furnish various 1cyanoalkyl isoquinolines 20 (Scheme 8). 10 mol % of Fe(OTf) 2 catalyst and 70 mol % DBU base was found to be an ideal catalytic system.…”

Section: Iron Catalysismentioning

confidence: 99%

Recent Advances in the 3 d‐Transition‐Metal‐Catalyzed Synthesis of Isoquinolines and its Derivatives

Maikhuri,

Rawat,

Rawat

2023

Adv Synth Catal

View full text Add to dashboard Cite

The preservation of scarce rare earth metals, such as palladium, rhodium, iridium, and others, poses a significant challenge for humanity due to their limited availability. These rare earth metals might be replaced by earth‐abundant 3d‐transition metals such as cobalt, manganese, iron, nickel, copper, etc. Isoquinolines have acquired an important position in synthetic organic chemistry as well as medicinal chemistry. They manifest in a diverse range of natural and synthetic molecules, serving as pivotal synthons for the synthesis of numerous bioactive compounds with notable medicinal significance. Numerous reports on the synthesis of isoquinoline derivatives via transition metal catalysis have been published worldwide. In this review, we summarize recent approaches for synthesizing various isoquinoline derivatives using 3d‐transition‐metal catalysts since 2020. The review has been divided into different 3d‐transition‐metal‐based catalysis. We expect that this review will bring a better overview of the present status of the significant progress made in the 3d‐transition‐metal‐based synthesis of isoquinolines and persuade more advancements and research in this area in the near future.

show abstract

An Iron‐Catalyzed Three‐Component Radical Cascade Cyclization to Access Cyanoalkylsulfonyl Quinolino‐Quinazolinones

Mohamathu Ghouse,

Tarun,

Maheswari

et al. 2024

Adv Synth Catal

View full text Add to dashboard Cite

An iron(II)‐catalyzed cascade reaction, involving cyanoalkylsulfonylation and cyclization, has been devised to enable the synthesis of functionalized sulfonylated quinolino‐quinazolinone alkyl nitriles. This three‐component radical transformation exhibits excellent chemo‐ and regioselectivity while functioning without the need for external oxidizing or reducing agents. The cost‐effectiveness of this catalytic system, together with its broad substrate application, which includes drug molecule derivatives, make this approach efficient and adaptable.

show abstract

Iron-catalyzed radical cascade cyclization of oxime esters with isocyanides: synthesis of 1-cyanoalkyl isoquinolines and 6-cyanoalkyl phenanthridines

Abstract: An iron-catalyzed radical cascade cyclization of oxime esters with isocyanides for synthesis of 1-cyanoalkyl isoquinolines and 6-cyanoalkyl phenanthridines has been developed. It demonstrated excellent functional group tolerance and broad substrate...

Cited by 8 publications

References 54 publications

Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters

Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters

Recent Advances in the 3 d‐Transition‐Metal‐Catalyzed Synthesis of Isoquinolines and its Derivatives

An Iron‐Catalyzed Three‐Component Radical Cascade Cyclization to Access Cyanoalkylsulfonyl Quinolino‐Quinazolinones

Contact Info

Product

Resources

About