Selective Reduction of β-Keto Amides to α,β-Unsaturated Olefinic Amides and β-Hydroxy Amides by Using Sodium Borohydride as the Reductant

陈翠,; 徐松森,; 刘卫兵,

doi:10.6023/cjoc201603020

Cited by 3 publications

(1 citation statement)

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“…However, in the presence of 1 equiv. of KOH, ( E )‐crotonamides 419 became the major products (Scheme 86a) [186] . In the presence of 20 mol% of MnCl 2 , the reduction of 420 afforded erythro ‐ 421 with excellent selectivity (Scheme 86b) [187] .…”

Section: Reactivities Of β‐Keto Amidesmentioning

confidence: 99%

β‐Keto Amides: A Jack‐of‐All‐Trades Building Block in Organic Chemistry

Zheng

et al. 2021

Eur J Org Chem

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β‐Keto amides are a versatile class of compounds that find wide applications in organic chemistry owing to the juxtaposition of multiple reaction sites within their molecular structures. Due to the importance of β‐keto amides in modern organic chemistry, numerous novel preparation methods, synthetic applications and unprecedented reactivities have been recorded over the past decade. Taking advantage of transition‐metal‐catalysis and organocatalysis, β‐keto amides have emerged into a jack‐of‐all‐trades building block for many stereoselective or tandemized multicomponent reactions. But so far, no reviews have been documented on these recent achievements with β‐keto amides. Our Review aims to provide a thorough summary regarding: (a) the synthesis of β‐keto amides, (b) the reactivities of β‐keto amides, (c) the synthetic applications of β‐keto amides in various important heterocyclic compounds, and (d) the coordination of β‐keto amides with main group elements and transition metals and the relevant applications.

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Section: Reactivities Of β‐Keto Amidesmentioning

confidence: 99%

β‐Keto Amides: A Jack‐of‐All‐Trades Building Block in Organic Chemistry

Zheng

et al. 2021

Eur J Org Chem

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TBHP Mediated C–N Bond Cleavage of Tertiary Amines toward the Synthesis of Oxalamides and α,β-Epoxy Amides

Zhang,

Zhu,

Xiao

et al. 2024

J. Org. Chem.

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An efficient and convenient method for the synthesis of oxalamides by the reaction of β-ketoamides with tertiary amines and TBHP was developed. A variety of β-ketoamides and tertiary amines substrates were well-tolerated in this transformation. Based on the control experiments, a plausible mechanism for this reaction was proposed that involved the tandem oxidation/amination process. In addition, α,β-epoxy amides could be obtained by adjusting the reaction conditions.

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Synthesis and fungicidal activity of 2-(methylthio)-4-methylpyrimidine carboxamides bearing a carbamate moiety

Zhang

Sun

et al. 2023

Phosphorus, Sulfur, and Silicon and the Related Elements

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Selective Reduction of β-Keto Amides to α,β-Unsaturated Olefinic Amides and β-Hydroxy Amides by Using Sodium Borohydride as the Reductant

Cited by 3 publications

References 0 publications

β‐Keto Amides: A Jack‐of‐All‐Trades Building Block in Organic Chemistry

β‐Keto Amides: A Jack‐of‐All‐Trades Building Block in Organic Chemistry

TBHP Mediated C–N Bond Cleavage of Tertiary Amines toward the Synthesis of Oxalamides and α,β-Epoxy Amides

Synthesis and fungicidal activity of 2-(methylthio)-4-methylpyrimidine carboxamides bearing a carbamate moiety

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