Rh(III)-catalyzed oxidative synthesis of pyrazoles from azomethines and acrylamides

Zhen, Wencui; Du, Zhengyin; Li, Xingwei

doi:10.1016/s1872-2067(12)60584-1

Cited by 7 publications

(1 citation statement)

References 48 publications

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“…In sharp contrast to the Rh(III)‐catalyzed [5 + 1] annulation between azomethine imines and acrylates, 47 Li et al demonstrated the [3 + 2] oxidative annulation reaction using acrylamides under similar reaction conditions. In this reaction, the authors suggested that the activation of the vinylic C–H bond on acrylamides served as the key initial step.…”

Section: Introductionmentioning

confidence: 99%

Tandem annulation and dipolar cycloaddition of azomethine imines in catalytic C(sp²)–H functionalization

Mishra,

Rakshit,

Moon

et al. 2023

Bulletin Korean Chem Soc

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The synthesis and functionalization of privileged nitrogen heterocycles has emerged as a central topic in drug discovery and material science. In this context, the tandem C–H functionalization and intramolecular annulation has received prodigious attention, as it is able to expedite the construction of heteroaromatic frameworks beyond conventional C–H functionalization. In general, significant effort has been made to develop the [3 + 2] dipolar cycloaddition of azomethine imines with π‐unsaturated compounds. Moreover, the [3 + 3], [4 + 3], [3 + 2 + 2], and [5 + 3] cycloaddition reactions of azomethine imines with various dipolarophiles have been demonstrated. To date, however, the combination of catalytic C–H functionalization and intramolecular cyclization using azomethine imines as both directing groups and dipolar units has been less explored. This review focuses on recent progress toward the catalytic tandem C–H functionalization and dipolar cycloaddition of azomethines imines with a range of coupling partners.

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Section: Introductionmentioning

confidence: 99%

Tandem annulation and dipolar cycloaddition of azomethine imines in catalytic C(sp²)–H functionalization

Mishra,

Rakshit,

Moon

et al. 2023

Bulletin Korean Chem Soc

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RhCl(CO)(PPh 3 ) 2 catalyzed α-alkylation of ketones with alcohols

Wang

Huang

et al. 2017

Journal of Organometallic Chemistry

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Rh(III)-catalyzed oxidative amidation of aldehydes: An efficient route to N-pyridinamides and imides

Dai

Liu

Tong

et al. 2014

Chinese Journal of Catalysis

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Rh(III)-catalyzed oxidative synthesis of pyrazoles from azomethines and acrylamides

Cited by 7 publications

References 48 publications

Tandem annulation and dipolar cycloaddition of azomethine imines in catalytic C(sp²)–H functionalization

Tandem annulation and dipolar cycloaddition of azomethine imines in catalytic C(sp²)–H functionalization

RhCl(CO)(PPh 3 ) 2 catalyzed α-alkylation of ketones with alcohols

Rh(III)-catalyzed oxidative amidation of aldehydes: An efficient route to N-pyridinamides and imides

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Rh(III)-catalyzed oxidative synthesis of pyrazoles from azomethines and acrylamides

Cited by 7 publications

References 48 publications

Tandem annulation and dipolar cycloaddition of azomethine imines in catalytic C(sp2)–H functionalization

Tandem annulation and dipolar cycloaddition of azomethine imines in catalytic C(sp2)–H functionalization

RhCl(CO)(PPh 3 ) 2 catalyzed α-alkylation of ketones with alcohols

Rh(III)-catalyzed oxidative amidation of aldehydes: An efficient route to N-pyridinamides and imides

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Tandem annulation and dipolar cycloaddition of azomethine imines in catalytic C(sp²)–H functionalization

Tandem annulation and dipolar cycloaddition of azomethine imines in catalytic C(sp²)–H functionalization