KI-Catalyzed Oxidative Cyclization of Enamines and <sup><i>t</i></sup>BuONO to Access Functional Imidazole-4-Carboxylic Derivatives

Li, Yingchun; Qiu, Jixia; Gao, Peng; Zhai, Le; Bai, Zijing; Chen, Huai-Juan

doi:10.1021/acs.joc.2c01943

Cited by 5 publications

(4 citation statements)

References 42 publications

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“…The imidazole-4-carboxylic motif is the bioactive center of many natural products and has wide applications in organic synthesis and the pharmaceutical industry. 22 The one-pot method starting with alkynes and CO 2 includes multistep orthogonal tandem reactions and presents a facile alternative to conventional synthetic methods, which suffer from tedious multistep operation and the use of transition metal catalysts. 23…”

Section: Resultsmentioning

confidence: 99%

Simple pyrazoles as efficient organocatalysts for alkyne–CO₂ carboxylation and one-pot construction of heterocycles

Zhang,

Li,

Xing

et al. 2024

Org. Chem. Front.

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Section: Resultsmentioning

confidence: 99%

Simple pyrazoles as efficient organocatalysts for alkyne–CO₂ carboxylation and one-pot construction of heterocycles

Zhang,

Li,

Xing

et al. 2024

Org. Chem. Front.

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“…Chen et al [62] have witnessed a metal-free, KI-promoted [4 + 1] cyclization of enamine 59 and aminating agent t BuONO 60 to synthesize biologically valued imidazole-4-carboxylic derivatives 61 (Scheme 33). The methodology shows great potential for the substrate scope over various enamines to deliver the product 61 in moderate to good yields.…”

Section: Synthesis Of Imidazoles Through Cycloaddition Reactionsmentioning

confidence: 99%

“…Chen et al [62] . have witnessed a metal‐free, KI‐promoted [4+1] cyclization of enamine 59 and aminating agent t BuONO 60 to synthesize biologically valued imidazole‐4‐carboxylic derivatives 61 (Scheme 33).…”

Section: Synthesis Of Imidazolesmentioning

confidence: 99%

Recent Advancements in Strategies for the Synthesis of Imidazoles, Thiazoles, Oxazoles, and Benzimidazoles

Kant,

Patel,

Banerjee

et al. 2023

ChemistrySelect

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Nitrogen‐containing heterocycles such as imidazoles, thiazoles, and oxazoles play a significant role in the fields of biological and pharmaceutical chemistry. These compounds were widely used for agrochemical, pesticide, medicinal, and industrial applications. Due to the wide spectrum of structural diversity as well as the biological and pharmaceutical activity of N‐heterocycles, a plethora of reports on their synthesis have appeared in the last few decades. However, developments in various bond‐forming strategies such as C−C, C−N, C−O, C−S, and N−N, as well as C−H activation, have been used as a powerful synthetic tool to derive copious N‐heterocycles. The most prominent and fascinating reports on the synthesis of imidazole, thiazole, oxazoles, and benzimidazole moieties by C−C and C−N coupling reactions, multi‐component and cycloaddition reactions, C−H activation, etc. are discussed in this study. These studies demonstrated the enormous potential of such methods for accelerating modern chemical synthesis and establishing molecular beauty through bonding. The various aspects of the methodologies, like optimized conditions, substrate scope, and mechanistic investigations, are discussed in detail.

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“…Enamines are readily available and versatile starting materials for heterocycle synthesis, such as 1,2,3-triazoles, imidazoles, pyridines, thiazoles, azirines, and indoles . Among these reports, the synthesis of pyrrolin-4-ones is of particular interest in the synthetic community.…”

Section: Introductionmentioning

confidence: 99%

Photooxidative Reaction of β-Oxoamides with Amines for the Synthesis of Pyrrolin-4-ones under External Photocatalyst-Free Conditions

Oyejobi,

Huang,

Luo

et al. 2024

J. Org. Chem.

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The incorporation of oxygen atoms from air under aerobic conditions plays an important role in organic synthesis. Herein, Brønsted acids are found to be a two-in-one strategic catalyst to transform enamines from β-oxoamides and amines to pyrrolin-4-ones without an external photocatalyst under visible-light conditions. The Brønsted acid can inhibit the C−C bond fragmentation of the [2 + 2] adduct from enamine and 1 O 2 , but most importantly, it can form photosensitizers with enamine and pyrrolin-4-one product by acidochromism to promote the 1 O 2 generation.

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KI-Catalyzed Oxidative Cyclization of Enamines and ^tBuONO to Access Functional Imidazole-4-Carboxylic Derivatives

Cited by 5 publications

References 42 publications

Simple pyrazoles as efficient organocatalysts for alkyne–CO₂ carboxylation and one-pot construction of heterocycles

Simple pyrazoles as efficient organocatalysts for alkyne–CO₂ carboxylation and one-pot construction of heterocycles

Recent Advancements in Strategies for the Synthesis of Imidazoles, Thiazoles, Oxazoles, and Benzimidazoles

Photooxidative Reaction of β-Oxoamides with Amines for the Synthesis of Pyrrolin-4-ones under External Photocatalyst-Free Conditions

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KI-Catalyzed Oxidative Cyclization of Enamines and tBuONO to Access Functional Imidazole-4-Carboxylic Derivatives

Cited by 5 publications

References 42 publications

Simple pyrazoles as efficient organocatalysts for alkyne–CO2 carboxylation and one-pot construction of heterocycles

Simple pyrazoles as efficient organocatalysts for alkyne–CO2 carboxylation and one-pot construction of heterocycles

Recent Advancements in Strategies for the Synthesis of Imidazoles, Thiazoles, Oxazoles, and Benzimidazoles

Photooxidative Reaction of β-Oxoamides with Amines for the Synthesis of Pyrrolin-4-ones under External Photocatalyst-Free Conditions

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Product

Resources

About

KI-Catalyzed Oxidative Cyclization of Enamines and ^tBuONO to Access Functional Imidazole-4-Carboxylic Derivatives

Simple pyrazoles as efficient organocatalysts for alkyne–CO₂ carboxylation and one-pot construction of heterocycles

Simple pyrazoles as efficient organocatalysts for alkyne–CO₂ carboxylation and one-pot construction of heterocycles