A Convenient One-Pot Method for the Synthesis of N-Methoxy-N-methyl Amides from Carboxylic Acids

Kim, Joong Gon; Jang, Doo Ok

doi:10.5012/bkcs.2010.31.01.171

Cited by 12 publications

(5 citation statements)

References 33 publications

(9 reference statements)

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“…SKM13 and SKM14 were synthesized using the following scheme: (1) the coupling of 4,7-dichloroquinoline and phenylalanine [ 23 ]; (2) the formation of Weinreb amide [ 24 ]; (3) reduction to aldehyde [ 25 ]; (4) Horner–Wadsworth–Emmons reaction with the amide phosphonate [ 26 ]. The chemical structures were confirmed by proton NMR.…”

Section: Methodsmentioning

confidence: 99%

Anti-malarial effect of novel chloroquine derivatives as agents for the treatment of malaria

Yeo

Liu

Kim

et al. 2017

Malar J

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BackgroundThe widespread emergence of anti-malarial drug resistance has necessitated the discovery of novel anti-malarial drug candidates. In this study, chloroquine derivatives were evaluated for the improved anti-malarial activity.ResultsNovel two derivatives (SKM13 and SKM14) were synthesized based on the chloroquine (CQ) template containing modified side chains such as α,β-unsaturated amides and phenylmethyl group. The selective index indicated that SKM13 was 1.28-fold more effective than CQ against the CQ-resistant strain Plasmodium falciparum. An in vivo mouse study demonstrated that SKM13 (20 mg/kg) could completely inhibit Plasmodium berghei growth in blood and increased the survival rate from 40 to 100% at 12 days after infection. Haematological parameters [red blood cell (RBC) count, haemoglobin level, and haematocrit level] were observed as an indication of clinical malarial anaemia during an evaluation of the efficacy of SKM13 in a 4-day suppression test. An in vivo study showed a decrease of greater than 70% in the number of RBC in P. berghei-infected mice over 12 days, but the SKM13 (20 mg/kg)-treated group showed no loss of RBC.ConclusionsCQ derivatives with substituents such as α,β-unsaturated amides and phenylmethyl group have enhanced anti-malarial activity against the CQ-resistant strain P. falciparum, and SKM13 is an excellent anti-malarial drug candidate in mice model.Electronic supplementary materialThe online version of this article (doi:10.1186/s12936-017-1725-z) contains supplementary material, which is available to authorized users.

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Section: Methodsmentioning

confidence: 99%

Anti-malarial effect of novel chloroquine derivatives as agents for the treatment of malaria

Yeo

Liu

Kim

et al. 2017

Malar J

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“…This compound was synthesised by adapting a previously described protocol. 50,51 To a cooled solution of the compound 30 (1 eq., 0.145 mmol, 50 mg) in anhydrous dichloromethane (3 mL), thionyl chloride was added dropwise under stirring (7 eq., 1.016 mmol, 73 μL). The solution was then stirred at room temperature for 3 h. The reaction was cooled at 0 °C before adding N , N -diisopropylethylamine dropwise (4 eq., 0.58 mmol, 0.101 mL), followed by N , O -dimethylhydroxylamine (2 eq., 0.290 mmol, 28 mg).…”

Section: Methodsmentioning

confidence: 99%

Computationally driven design of an artificial metalloenzyme using supramolecular anchoring strategies of iridium complexes to alcohol dehydrogenase

2022

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“…In 2010, Jang and co-workers 14 describeda flexible one-pot process for the synthesis of Weinreb amides from carboxylic acids using trichloroacetonitrile (TCA) and triphenylphosphine (TPP) (Scheme 1). Here, the authors presumed that carboxylic acid chlorides generated in situthrougha combination of carboxylic acids 1 with TCA and TPP, followed by treatment with N,O-dimethylhydroxylamine in the presence of triethylamine (TEA) to produce the corresponding Weinreb amides.…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, Herr and co-workers 17 detailed the efficient role of palladium-catalyst in preparation of benzamides 16 and α,β-unsaturated Weinreb amides 15 using organoboronic acids (12 or 13) and N-methyl-N-methoxy carbamoyl chloride substrate 14 conditions, using potassium phosphate monohydrate as a base and dry ethanol as a solvent at 65 o C, the key incorporation between the substrates with the palladium catalyst, confirmed one-pot synthesis of the expected products. Variety of aromatic organoboronic acids bearing electron-withdrawing and electron-donating groups, displayed a wide manner toward the reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Recent Developments in Weinreb Synthesis and Their Applications

Khalid

Mohammed

Kalo³

2019

Orient. J. Chem

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N-methoxy-N-methyl amides or Weinreb amides are worthy embranchment of amide group and their rich functional groups in organic synthesis become a strong else unfeasible conversion. Weinreb amides are produced as an intermediate product of the reaction of carboxylic acids, acid chloride or esters with organometallic reagents, which was first uncovered in 1981. The direct conversion of carboxylic acids or acid chlorides or esters to ketones or aldehydes using organometallic reagents do not lead in high yields, because the intermediate ketones are still highly reactive toward the organometallic reagent. However, after derivatization to the corresponding Weinreb Amide, reaction with organometallics does give the desired ketones, as the initial adduct is stabilized and doesn't undergo further reactions. A nucleophilic addition to the Weinreb amides results in a unique and stable five-membered cyclic tetrahedral intermediate which protects the over-addition, leading to a selective conversion.

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A Convenient One-Pot Method for the Synthesis of N-Methoxy-N-methyl Amides from Carboxylic Acids

Cited by 12 publications

References 33 publications

Anti-malarial effect of novel chloroquine derivatives as agents for the treatment of malaria

Anti-malarial effect of novel chloroquine derivatives as agents for the treatment of malaria

Computationally driven design of an artificial metalloenzyme using supramolecular anchoring strategies of iridium complexes to alcohol dehydrogenase

Recent Developments in Weinreb Synthesis and Their Applications

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