Electrochemical Oxidative Regioselective C–H Cyanation of Imidazo[1,2-<i>a</i>]pyridines

Cui, Ting; Zhan, Yanling; Dai, Changhui; Lin, Jun; Liu, Ping; Sun, Peipei

doi:10.1021/acs.joc.0c03026

Cited by 30 publications

(18 citation statements)

References 50 publications

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“…Finding an efficient and practical method for cyanation of more complex heterocycle, e. g., imidazopyridine is even more difficult work. Liu and Sun et al [19] . very recently (in 2021) reported an electrochemical oxidative C−H cyanation of imidazopyridines 1 using TMSCN 13 as the cyano source to synthesize C‐3 cyanated products 14 (Scheme 7).…”

Section: Electrochemical Functionalization Of Imidazopyridinementioning

confidence: 99%

Electrochemical Functionalization of Imidazopyridine and Indazole: An Overview

Ghosh¹,

Ghosh

Hajra

2021

Adv Synth Catal

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Electrochemical synthesis offers a mild, simple, and efficient tool for the preparation of interesting and useful molecules, thus eluding severe chemical oxidizing and reducing agents used in conventional synthetic methods. In particular, electrochemical C−H activation is expected to play an important role in the direct functionalization of heterocyclic compounds. Over the past few decades, the research interest in imidazopyridine and indazole has increased significantly due to their multipurpose uses in medicinal and industrial chemistry. Therefore, structural modification of these heterocycles using electro‐oxidation has become one of the important research topics among synthetic organic chemistry in recent time. This review provides a comprehensive discussion of electrochemical functionalization of indazoles and imidazopyridines published so far. A summary of the current challenges and the future direction for the development of efficient and green electrochemical methods for functionalization of these heterocycles is also presented.

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Section: Electrochemical Functionalization Of Imidazopyridinementioning

confidence: 99%

Electrochemical Functionalization of Imidazopyridine and Indazole: An Overview

Ghosh¹,

Ghosh

Hajra

2021

Adv Synth Catal

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“…[33] Regioselective C-3 cyanation of imidazo[1,2-a] pyridine core is reported previously. [34] However, directed cyanation at ortho position of 2-arylimidazo[1,2-a]pyridine is rare. Song & Hao et al [35] first reported ortho biscyanation of 2-arylimidazo[1,2-a]pyridines (24 a) assisted by N-directed ortho double CÀ H activation using N-cyano-N-phenylp-methylbenzenesulfonamide (NCTS) (24 b) as a cyanating agent.…”

Section: Cyanationmentioning

confidence: 99%

Ortho C−H Functionalization of 2‐Arylimidazo[1,2‐a]pyridines

Ghosh

Laru

Hajra

2021

The Chemical Record

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C−H activation and functionalization is quite promising in recent days as the strategy offers a go‐to general method for different bond formations and hence grants synthetic versatility. At the same time, imidazopyridine, a fused bicycle of imidazole moiety with pyridine ring, has a profound impact due to its ubiquitous and prodigious application in medicinal as well as material chemistry. The presence of N‐1 atom in 2‐arylImidazo[1,2‐a]pyridine facilitates the coordination with metal catalysts leading to the formation of ortho‐substituted products. This review summarizes all the articles on ortho C−H functionalization of 2‐arylImidazo[1,2‐a]pyridines published till August 2021.

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“…Using N -hydroxybenzimidoyl chloride ester (NHBC) to activate amino acids, Wang et al enabled a leaving-group-assisted decarboxylative coupling of amino acids with heteroarenes (Scheme c). In continuation of our study on the direct C–H functionalization of heteroarenes, we herein disclose the aminoalkylation of quinoxalinones and some other heterocycles by the decarboxylative coupling of α-amino acids under photoredox conditions in air (Scheme d).…”

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confidence: 93%

Visible-Light-Induced C–H Bond Aminoalkylation of Heterocycles by the Decarboxylation Coupling of Amino Acids

Dai

Xie

et al. 2021

Org. Lett.

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An efficient visible-light-induced decarboxylative coupling reaction of N-protecting α-amino acids with heterocycles for the generation of aminoalkylated heterocycles is presented. A series of aminoalkylated heterocycles were obtained in moderate to good yields. Attractive features of this process include the generation of aminomethyl radical by an inexpensive organic photocatalyst under transition-metal-free conditions.

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Electrochemical Oxidative Regioselective C–H Cyanation of Imidazo[1,2-a]pyridines

Cited by 30 publications

References 50 publications

Electrochemical Functionalization of Imidazopyridine and Indazole: An Overview

Electrochemical Functionalization of Imidazopyridine and Indazole: An Overview

Ortho C−H Functionalization of 2‐Arylimidazo[1,2‐a]pyridines

Visible-Light-Induced C–H Bond Aminoalkylation of Heterocycles by the Decarboxylation Coupling of Amino Acids

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