One-pot synthesis of amides from carboxylic acids activated using thionyl chloride

Leggio, Antonella; Belsito, Emilia Lucia; G, De Luca; Gioia, Maria Luisa Di; Leotta, V.; Romio, Emanuela; Siciliano, Carlo; Liguori, Angelo

doi:10.1039/c5ra24527c

Cited by 69 publications

(45 citation statements)

References 40 publications

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“…While the mechanism of the reaction is unclear at this moment, we proposed that the 2‐nitrobenzoic N , N ‐dimethylcarbamothioic anhydride intermediate may be firstly formed by the direct coupling of the acid with the TMTD in the presence of PPh 3 . Then, the anhydride intermediate undergo a decarboxylation (decarbonylsulfide, ‐COS) process leading to the desired amide product ,,, Further studies on the details of the mechanism and the related applications for this protocol are undergoing in our lab.…”

Section: Resultsmentioning

confidence: 99%

Phosphine‐Promoted Amide Bond Formation Reactions from Carboxylic Acids and Tetraalkylthiuram Disulfides

Cheng

Tang

et al. 2018

ChemistrySelect

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An efficient protocol for the straightforward synthesis of amides from readily available carboxylic acids and tetraalkylthiuram disulfides is presented. The reaction proceeds through direct cross‐coupling reactions promoted by catalytic amount of PPh3 in DMSO. This protocol is compatible with a wide variety of electron‐donating and ‐withdrawing acids, which shows its practical synthetic value in organic synthesis.

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Section: Resultsmentioning

confidence: 99%

Phosphine‐Promoted Amide Bond Formation Reactions from Carboxylic Acids and Tetraalkylthiuram Disulfides

Cheng

Tang

et al. 2018

ChemistrySelect

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“…The Schiff base derivatives deduced from amino acid are stable compounds, they were prepared by stirring Schiff bases with an appropriate primary or secondary amines to study the effect of imine and amide moieties on the antimicrobial activity. As shown in (Scheme 1), the reaction of Schiff base 3 with the corresponding primary or secondary amino compounds in the presence of SOCl 2 and Et 3 N gave compounds 4-11 according to previously reported procedure [Leggio et al, 2016]. All these compounds were obtained in good yields (62-74).…”

Section: ) Chemistrymentioning

confidence: 87%

“…The preparation of compounds 4-11 by a one-pot reaction was according to a reported method [Leggio et al, 2016]. To a solution of compound 3 (1 mmol), an appropriate primary or secondary amine (1 mmol) and triethylamine (3 mmol) in DCM, SOCl 2 (1 mmol) was added dropwise with stirring and cooling.…”

Section: General Procedures For the Synthesis Of Compounds 4-11mentioning

confidence: 99%

Design, Synthesis and Ev0aluation of Some New Schiff Base Derivatives as Potential Antimicrobial Agents

Sherbiny

2017

Al-Azhar Journal of Pharmaceutical Sciences

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In a trial to discover potential antimicrobial agents against the increasing microbial resistance, eight new Schiff base derivatives of glycine amino acid obtained from the condensation reaction with benzaldehyde were designed and synthesized by conventional approach. The structures of all the synthesized compounds were elucidated using IR, 1 H NMR and 13 C NMR along with MS spectra data. In addition, the antimicrobial activities of the new compounds were screened with gentamycin and ketoconazole as the control against four significant representative strains including Staphylococcus aureus, Escherichia coli, Aspergillus niger, and Candida albicans, using broth microdilution method. The antimicrobial activity results revealed that most of the tested compounds exhibited significant antibacterial activity. In particularly, compound 5 was found to be the most potent antibacterial agent with MIC value of 18 exhibiting better activity against Staphylococcus aureus than Escherichia coli. Additionally, compounds 4, 6, and 10 displayed potent antibacterial activity with MIC value of 15, 16, and 16 respectively. However, compounds 10 and 11 showed good activity against both bacterial strains along with Aspergillus niger, indicating their broad spectrum of activity. The structure-activity relationship analysis suggested that the electronic and lipophilic factors of aromatic substituents on the amide nitrogen significantly contributed to antibacterial activity. Moreover, the presence of aromatic heterocyclic or heterobicyclic containing more nitrogen atoms considerably influenced the antifungal activity.

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“…The basic of spectroscopic analysis is the evaluation of the nuclei behavior that underwent an inhomogeneous external field, which perturbs the equilibrium in a steady uniform magnetic field. In fact, at equilibrium, nuclei are distributed among the energy levels according to the Boltzmann distribution with a specific net magnetization vector, but this state can be disrupted by the absorption of radio-frequency energy such as that caused by a NMR instrument [21]. After the removal of the disruption field, the nuclear spin system returns to its equilibrium state and the transverse component of the magnetization vector exponentially decays.…”

Section: Nuclear Magnetic Resonance Measurements-t 2 Relaxation Time mentioning

confidence: 99%

A Study of Rubber-REOB Extender to Produce Sustainable Modified Bitumens

et al. 2020

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Thanks to greater attention to the environment and the depletion of non-renewable resources, the sustainability and the circular economy have become crucial topics. The current trend of pavement engineering is to reduce the use of standard bitumen by replacing it with more sustainable materials such as industrial residues and by-products. In this regard, the present study aims to characterize innovative extended bitumen using recycled materials. Due to promising preliminary results as bitumen modifiers, the powdered rubber from end-of-life tires and the re-refined engine oil bottom (REOB) have been investigated as feasible components of bitumen extenders. Nevertheless, several variables strongly affect the performance of the resulting binder, which cannot be neglected. Hence, this research focuses on the rubber-REOB interaction in order to evaluate their optimum ratio, which may maximize the use and advantages of both recycled materials as suitable partial replacements for bitumen. Various rubber-REOB ratios were considered and investigated by means of low and high frequency nuclear magnetic resonance (NMR) spectrometers and scanning electron microscope (SEM).

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One-pot synthesis of amides from carboxylic acids activated using thionyl chloride

Abstract: We report on a one-pot synthesis of secondary and tertiary amides from carboxylic acids and amines in the presence of a tertiary amine by using thionyl chloride.

Cited by 69 publications

References 40 publications

Phosphine‐Promoted Amide Bond Formation Reactions from Carboxylic Acids and Tetraalkylthiuram Disulfides

Phosphine‐Promoted Amide Bond Formation Reactions from Carboxylic Acids and Tetraalkylthiuram Disulfides

Design, Synthesis and Ev0aluation of Some New Schiff Base Derivatives as Potential Antimicrobial Agents

A Study of Rubber-REOB Extender to Produce Sustainable Modified Bitumens

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