A metal-free approach for transamidation of amides with amines in aqueous media

Srinivas, M.; Hudwekar, Abhinandan D.; Venkateswarlu, Vunnam; Reddy, G. Lakshma; Kumar, K. Raghavendra; Vishwakarma, Ram A.; Sawant, Sanghapal D.

doi:10.1016/j.tetlet.2015.06.052

Cited by 40 publications

(15 citation statements)

References 35 publications

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“…In addition to these metal-free strategies for transamidation, the use of K 2 S 2 O 8 in aqueous media was recently described [ 47 ]. The reaction can be performed under the influence of microwaves or conventional heating.…”

Section: Other Catalystsmentioning

confidence: 99%

Direct Transamidation Reactions: Mechanism and Recent Advances

2018

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Amides are undeniably some of the most important compounds in Nature and the chemical industry, being present in biomolecules, materials, pharmaceuticals and many other substances. Unfortunately, the traditional synthesis of amides suffers from some important drawbacks, principally the use of stoichiometric activators or the need to use highly reactive carboxylic acid derivatives. In recent years, the transamidation reaction has emerged as a valuable alternative to prepare amides. The reactivity of amides makes their direct reaction with nitrogen nucleophiles difficult; thus, the direct transamidation reaction needs a catalyst in order to activate the amide moiety and to promote the completion of the reaction because equilibrium is established. In this review, we present research on direct transamidation reactions ranging from studies of the mechanism to the recent developments of more applicable and versatile methodologies, emphasizing those reactions involving activation with metal catalysts.

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Section: Other Catalystsmentioning

confidence: 99%

Direct Transamidation Reactions: Mechanism and Recent Advances

2018

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“…One of the most interesting protocols is using N,Ndimethylformamide (DMF) to produce N-formyl compounds. [6][7][8] For example, imidazole and DMF (N,N-dimethylformamide); [9] P2O5 and DMF; [10] POCl3 and DMF; [11] [Ni(quin)2], DMF and imidazole. [12] Microwave irradiation can also assist the N-formylation.…”

Section: Introductionmentioning

confidence: 99%

N‐Formylation of amines using a domestic microwave oven and bioactivities of some N‐formamides

Mai,

Van Dat,

Huan

et al. 2021

Vietnam Journal of Chemistry

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A reasonable and chemoselective approach for N‐formylation of various amines with N,N‐dimethylformamide in presence of acetic acid has been improved under irradiation of a domestic microwave oven. The method was found to be compatible with primary, secondary, aromatic and aliphatic amines with electron withdrawing and electron donating groups as well but did not support to form N‐formate derivatives. N‐formamides 1, 2, and 3 did not exhibit antibacterial activity on Gram(+), Gram(‐) and fungi but compounds 1, 2, 18 and 19 showed weak antioxidant activity with SC: 36.8 %, 38.3 %, 45.7 %, respectively. Compound 18 exhibited antioxidant activity with SC50: 47.2 μg/mL.

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“…[1] Few vital drug molecules possessing amide moiety are shown in Figure 1. [2][3][4][5] Importantly, the amide bond formation has been recognized as the most commonly employed chemical reaction in the industries. Over the years, several methods have been documented in the literature for amide bond formation.…”

Section: Introductionmentioning

confidence: 99%

Graphene Oxide as a Metal‐free Carbocatalyst for Direct Amide Synthesis from Carboxylic Acid and Amine Under Solvent‐Free Reaction Condition

2020

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Herein, a highly efficient, metal‐free, carbocatalyst, graphene oxide (GO) has been screened for the direct amidation of carboxylic acids with amines. The present catalytic system accessed a broad range of substrates to afford amides in excellent yields. A plausible reaction mechanism involving H‐bonding with the reactants is described. Furthermore, the GO can be recycled and reused up to five cycles without substantial loss in catalytic activity.

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A metal-free approach for transamidation of amides with amines in aqueous media

Cited by 40 publications

References 35 publications

Direct Transamidation Reactions: Mechanism and Recent Advances

Direct Transamidation Reactions: Mechanism and Recent Advances

N‐Formylation of amines using a domestic microwave oven and bioactivities of some N‐formamides

Graphene Oxide as a Metal‐free Carbocatalyst for Direct Amide Synthesis from Carboxylic Acid and Amine Under Solvent‐Free Reaction Condition

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