Atom economical synthesis of N-alkylbenzamides via the iron(<scp>iii</scp>) sulfate catalyzed rearrangement of 2-alkyl-3-aryloxaziridines in water and in the presence of a surfactant

Kraı̈em, Jamil; Ollevier, Thierry

doi:10.1039/c6gc03589b

Cited by 25 publications

(12 citation statements)

References 42 publications

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“…Amides, as one of the most important classes of N-containing organic compounds, are known to be present in proteins, natural products, bioactive compounds, and agrochemicals . In recent years, constant efforts have targeted efficient catalytic methods for the construction of the omnipresent amide bond . Despite significant advancement in this area, there is still a continuing need for development of new synthetic methods for amide bond synthesis.…”

Section: Resultsmentioning

confidence: 99%

Vanadium-Catalyzed Oxidative C(CO)–C(CO) Bond Cleavage for C–N Bond Formation: One-Pot Domino Transformation of 1,2-Diketones and Amidines into Imides and Amides

et al. 2017

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A novel vanadium-catalyzed one-pot domino reaction of 1,2-diketones with amidines has been identified that enables their transformation into imides and amides. The reaction proceeds by dual acylation of amidines via oxidative C(CO)-C(CO) bond cleavage of 1,2-diketones to afford N,N'-diaroyl-N-arylbenzamidine intermediates. In the reaction, these intermediates are easily hydrolyzed into imides and amides through vanadium catalysis. This method provides a practical, simple, and mild synthetic approach to access a variety of imides as well as amides in high yields. Moreover, one-step construction of imide and amide bonds with a long-chain alkyl group is an attractive feature of this protocol.

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Section: Resultsmentioning

confidence: 99%

Vanadium-Catalyzed Oxidative C(CO)–C(CO) Bond Cleavage for C–N Bond Formation: One-Pot Domino Transformation of 1,2-Diketones and Amidines into Imides and Amides

et al. 2017

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“…Very recently, Ollevier and co-workers also reported that in the presence of SDS, iron(III) sulfate could catalyze the rearrangement of 2-alkyl-3-aryloxaziridines in water to afford the desired N -alkylbenzamides in excellent yield (Scheme ). The reaction only afforded the products in low yield without SDS, even at raised temperatures. The authors also compared the atom economy and the generated waste to those reported previously.…”

Section: Surfactant-based Catalystsmentioning

confidence: 99%

Catalytic Organic Reactions in Water toward Sustainable Society

et al. 2017

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Traditional organic synthesis relies heavily on organic solvents for a multitude of tasks, including dissolving the components and facilitating chemical reactions, because many reagents and reactive species are incompatible or immiscible with water. Given that they are used in vast quantities as compared to reactants, solvents have been the focus of environmental concerns. Along with reducing the environmental impact of organic synthesis, the use of water as a reaction medium also benefits chemical processes by simplifying operations, allowing mild reaction conditions, and sometimes delivering unforeseen reactivities and selectivities. After the "watershed" in organic synthesis revealed the importance of water, the development of water-compatible catalysts has flourished, triggering a quantum leap in water-centered organic synthesis. Given that organic compounds are typically practically insoluble in water, simple extractive workup can readily separate a water-soluble homogeneous catalyst as an aqueous solution from a product that is soluble in organic solvents. In contrast, the use of heterogeneous catalysts facilitates catalyst recycling by allowing simple centrifugation and filtration methods to be used. This Review addresses advances over the past decade in catalytic reactions using water as a reaction medium.

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“…Indeed, DMC is well-known as safe reagent and solvent that has been used for many green applications [ 31 – 33 ]. On the other hand, water is a simply and environmentally benign solvent and interest has increasingly turned to it as the greenest solvent of chemical reactions [ 34 ]. In order to find the best reaction conditions, a model reaction was chosen using (L)-alanine phenylhydrazide ( 3a , Scheme 3 ), and the results of these optimized studies were summarized in Table 2 .…”

Section: Resultsmentioning

confidence: 99%

Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

Bouzayani¹,

Kraїem²,

Marque³

et al. 2018

Beilstein J. Org. Chem.

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New chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-dione derivatives were obtained in good to excellent yields via the cyclocondensation of 2-formylbenzoic acid and various α-amino acid arylhydrazides using water as the solvent in the presence of sodium dodecyl sulfate as the surfactant and under simple and minimum manipulation, without purification. The reaction is totally diastereoselective and gives access to the nitrogenated tricyclic core with a relative trans stereochemistry.

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Atom economical synthesis of N-alkylbenzamides via the iron(iii) sulfate catalyzed rearrangement of 2-alkyl-3-aryloxaziridines in water and in the presence of a surfactant

Abstract: A green preparation of N-alkylbenzamides involves synthesis of 2-alkyl-3-aryloxaziridines from N-alkylamines and benzaldehydes followed by iron(iii) sulfate catalyzed rearrangement to the corresponding amides in water and in the presence of sodium dodecyl sulfate.

Cited by 25 publications

References 42 publications

Vanadium-Catalyzed Oxidative C(CO)–C(CO) Bond Cleavage for C–N Bond Formation: One-Pot Domino Transformation of 1,2-Diketones and Amidines into Imides and Amides

Vanadium-Catalyzed Oxidative C(CO)–C(CO) Bond Cleavage for C–N Bond Formation: One-Pot Domino Transformation of 1,2-Diketones and Amidines into Imides and Amides

Catalytic Organic Reactions in Water toward Sustainable Society

Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

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