Copper-catalyzed radical cascade cyclization: Synthesis of benzylated benzimidazo [2,1-a]isoquinoline-6(5H)-ones

Li, Zhenhua; Cao, Yingyan; Chen, Lijun; Rong, Dayou; Guo-qin, Huang; Xie, Yuanyuan

doi:10.1016/j.tet.2022.132952

Cited by 7 publications

(2 citation statements)

References 43 publications

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“…Based on the experimental results and previous reports, [8][9][10][11][12][13][14][15]17 a plausible mechanism for this transformation is proposed in Scheme 4. Firstly, the decomposition of TBHP upon heating forms the tert-butoxyl and tert-butyl peroxy radicals, which abstract an -H of the alcohol to form the intermediate A.…”

Section: Scheme 3 a Control Experimentsmentioning

confidence: 87%

A Metal-Free TBHP-Triggered Cascade Cyclization of 2-Arylindoles with Alcohols: Synthesis of Hydroxyalkylated Indolo[2,1-a]isoquinoline Derivatives

Li¹,

Tang²,

Xiang³

et al. 2022

Synlett

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A practical method for the synthesis of hydroxyalkylated indolo[2,1-a]isoquinoline derivatives through the metal-free cascade cyclization of 2-arylindoles with alcohols has been disclosed. The present method features transition-metal-free conditions and exceptional functional group tolerance. A series of valuable hydroxyalkylated indolo[2,1-a]isoquinoline derivatives bearing various functional groups were synthesized in moderate to excellent yields.

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Section: Scheme 3 a Control Experimentsmentioning

confidence: 87%

A Metal-Free TBHP-Triggered Cascade Cyclization of 2-Arylindoles with Alcohols: Synthesis of Hydroxyalkylated Indolo[2,1-a]isoquinoline Derivatives

Li¹,

Tang²,

Xiang³

et al. 2022

Synlett

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“…Zhang and coworkers [104] reported a protocol to synthesize cyano-containing benzimidazo Isaacs and coworkers [105] In 2020, Wang and coworkers [106] developed a protocol to synthesize a series of (benzo)imidazo A new methodology for synthesizing benzimidazo[2,1-a]isoquinolin-6(5H)-diones 206 via addition reaction of benzyl radical to N-methacryloyl-2-arylbenzoimidazoles 204 using DTBP oxidant under Cu-catalysis has been demonstrated by Li and coworkers (Scheme 70). [107] A varied range of substituents on both the reactants 204 and 205 were easily accommodated and various products 206 were furnished in good yields (up to 75%). The methodology provides advantages such as acid-/base-free reaction conditions, neat reaction conditions, and good substrate scope.…”

Section: Copper 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

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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.

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Six-membered ring systems: pyridines and benzo derivatives

Badenock

2023

Progress in Heterocyclic Chemistry

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Copper-catalyzed radical cascade cyclization: Synthesis of benzylated benzimidazo [2,1-a]isoquinoline-6(5H)-ones

Cited by 7 publications

References 43 publications

A Metal-Free TBHP-Triggered Cascade Cyclization of 2-Arylindoles with Alcohols: Synthesis of Hydroxyalkylated Indolo[2,1-a]isoquinoline Derivatives

A Metal-Free TBHP-Triggered Cascade Cyclization of 2-Arylindoles with Alcohols: Synthesis of Hydroxyalkylated Indolo[2,1-a]isoquinoline Derivatives

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

Six-membered ring systems: pyridines and benzo derivatives

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