One-Pot Synthesis of α-Ketoamides from α-Keto Acids and Amines Using Ynamides as Coupling Reagents

Ma, Jianting; Cui, Xuemin; Xu, Junyu; Tan, Yinfeng; Wang, Yan; Wang, Xuesong; Li, Youbin

doi:10.1021/acs.joc.1c02453

Cited by 14 publications

(7 citation statements)

References 85 publications

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“…From N -methyl- p -toluenesulfonamide ( 6a , 0.186 g, 1 mmol); white solid; yield: 0.226 g (99%); mp 49.5–51.5 °C (lit . 51–53 °C); R f = 0.10 (PE/EtOAc = 5:1).…”

Section: Experimental Sectionmentioning

confidence: 99%

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Ferric Chloride-Mediated Transacylation of N-Acylsulfonamides

Sang,

Dong,

et al. 2024

J. Org. Chem.

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Transacylation of N-acylsulfonamides, which replaces the N-acyl group with a new one, is a challenging and underdeveloped fundamental transformation. Herein, a general method for transacylation of N-acylsulfonamides is presented. The transformation is enabled by coincident catalytic reactivities of FeCl 3 for nonhydrolytic deacylation of N-acylsulfonamides and subsequent acylation of the resultant sulfonamides and can be conducted either stepwise or in a one-pot manner. GaCl 3 and RuCl 3 •xH 2 O are similarly effective for the reaction. This method is mild, efficient, and operationally simple. A variety of functional groups such as halogeno, keto, nitro, cyano, ether, and ester are well tolerated, providing the transacylation products in good to excellent yields.

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“…From N -methyl- p -toluenesulfonamide ( 6a , 0.186 g, 1 mmol); white solid; yield: 0.226 g (99%); mp 49.5–51.5 °C (lit . 51–53 °C); R f = 0.10 (PE/EtOAc = 5:1).…”

Section: Experimental Sectionmentioning

confidence: 99%

“…From N-methyl-p-toluenesulfonamide (6a, 0.186 g, 1 mmol); white solid; yield: 0.226 g (99%); mp 49.5−51.5 °C (lit. 83 51−53 °C); R f = 0.10 (PE/EtOAc = 5:1). 1 H NMR (400 MHz, CDCl 3 ): δ 7.77 (d, J = 8.4 Hz, 2H), 7.36 (d, J = 8.6 Hz, 2H), 3.28 (s, 3H), 2.45 (s, 3H), 2.39 (s, 3H).…”

Section: N-((benzo[d]isoxazol-3-ylmethyl)sulfonyl)acetamide (3x)mentioning

confidence: 99%

Ferric Chloride-Mediated Transacylation of N-Acylsulfonamides

Sang,

Dong,

et al. 2024

J. Org. Chem.

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“…More significantly, the potential utility of this protocol was demonstrated by the facile synthesis of carfilzomib with no column chromatography for the whole 12 steps. [59] Subsequently, the activity of Yanmides in the synthesis of thioamides/primary thioamides, [60] thiopeptides bond, [61] α-Ketoamides, [62] lactam and peptide fragment condensation [63] were further explored. Apart from the abovementioned ynamide-type coupling reagents, other triple bondcontaining reagents, including methyl propiolate (99, Figure 2, Scheme 19c) [64] and dimethyl dimethyl(prop-2-yn-1yl)sulfonium bromide (Yin, Wang & Li, 2022, Figure 2, Scheme 19d), [65] were also recently developed and applied to the field of SPPS.…”

Section: Direct Amidation Of Carboxylic Acids With Amines Promoted By...mentioning

confidence: 99%

Recent Advances in Carbon‐Nitrogen/Carbon‐Oxygen Bond Formation Under Transition‐Metal‐Free Conditions

Zhang

Song

Shi

et al. 2023

The Chemical Record

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Carbon‐heteroatom bond formation under transition‐metal free conditions provides a powerful synthetic alternative for the efficient synthesis of valuable molecules. In particular, C−N and C−O bonds are two important types of carbon‐heteroatom bonds. Thus, continuous efforts have been deployed to develop novel C−N/C−O bond formation methodologies involving various catalysts or promoters under TM‐free conditions, which enables the synthesis of various functional molecules comprising C−N/C−O bonds in a facile and sustainable manner. Considering the significance of C−N/C−O bond construction in organic synthesis and materials science, this review aims to comprehensively present selected examples on the construction of C−N (including amination and amidation) and C−O (including etherification and hydroxylation) bonds without transition metals. Besides, the involved promoters/catalysts, substrate scope, potential application and possible reaction mechanisms are also systematically discussed.

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“…Accordingly, in recent decades, there has been considerable focus on advancing traditional methods for constructing α-ketoamide motifs in synthetic organic chemistry . Consequently, various efforts have been made to devise novel and convenient approaches for accessing α-ketoamides, employing a spectrum of catalysts, including metals, nonmetals, organocatalysts, photocatalysts, and electrocatalysts (Scheme B). − …”

Section: Introductionmentioning

confidence: 99%

Electrochemical Formation of α-Ketoamides from Ketoximes through Non-Beckmann Mechanism Pathway

Yavari,

Shaabanzadeh

2024

J. Org. Chem.

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α-Ketoamides are highly valued in synthetic chemistry due to their incorporation into diverse natural products and drug molecules. Here, we present an innovative electrochemical approach for constructing α-ketoamides, utilizing a mild and environmentally friendly strategy in a user-friendly undivided cell setup under constant current. The excellent functional-group tolerance, convenient accessibility of reaction instruments and starting materials, and easy scalability collectively enhance the importance of this protocol compared to previous challenging methods. Additionally, mechanistic insight into this reaction is obtained through the investigation of cyclic voltammograms of the reactants.

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One-Pot Synthesis of α-Ketoamides from α-Keto Acids and Amines Using Ynamides as Coupling Reagents

Cited by 14 publications

References 85 publications

Ferric Chloride-Mediated Transacylation of N-Acylsulfonamides

Ferric Chloride-Mediated Transacylation of N-Acylsulfonamides

Recent Advances in Carbon‐Nitrogen/Carbon‐Oxygen Bond Formation Under Transition‐Metal‐Free Conditions

Electrochemical Formation of α-Ketoamides from Ketoximes through Non-Beckmann Mechanism Pathway

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