A Novel One-Pot Synthesis of Unsymmetrical Acyclic Imides

Habibi, Zohreh; Salehi, Peyman; Yousefi, Maryam

doi:10.1055/s-2007-970781

Synlett

2007

DOI: 10.1055/s-2007-970781

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A Novel One-Pot Synthesis of Unsymmetrical Acyclic Imides

Zohreh Habibi¹,

Peyman Salehi²,

Maryam Yousefi³

Abstract: A new and convenient method was found for the one-pot synthesis of symmetrical and unsymmetrical linear imides by reaction of aliphatic and aromatic nitriles with acyclic carboxylic anhydrides in the presence of silica sulfuric acid as an active and recyclable reagent.

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Cited by 4 publications

References 6 publications

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DMAPO/Boc₂O‐Mediated One‐Pot Direct N‐Acylation of Less Nucleophilic N‐Heterocycles with Carboxylic Acids

2023

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In contrast to the considerable progress in the development of methodologies for amide bond formation in amines, the development of direct N‐acylation of less nucleophilic N‐heterocycles and amides with carboxylic acids is still challenging. In this report, we describe the direct N‐acylation of less nucleophilic heterocycles and amides with carboxylic acids promoted by the 4‐(N,N‐dimethylamino)pyridine N‐oxide (DMAPO)/di‐tert‐butyl dicarbonate (Boc2O) system. The new one‐pot method, which does not involve pre‐activation of substrates, enables the direct N‐acylation of a wide variety of nitrogen nucleophiles such as indole, carbazole, pyrrole, pyrazole, lactam, oxazolidinone, and anilide with carboxylic acids in high yield. The new method also exhibits excellent functional group tolerance and broad substrate scope. As the present method is practical, operationally simple, and scalable, it should find wide applications in both academic and industrial laboratories.

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DMAPO/Boc₂O‐Mediated One‐Pot Direct N‐Acylation of Less Nucleophilic N‐Heterocycles with Carboxylic Acids

2023

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Chemoselective Acylation of Primary Amines and Amides with Potassium Acyltrifluoroborates under Acidic Conditions

et al. 2017

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Current methods for constructing amide bonds join amines and carboxylic acids by dehydrative couplings-processes that usually require organic solvents, expensive and often dangerous coupling reagents, and masking other functional groups. Here we describe an amide formation using primary amines and potassium acyltrifluoroborates promoted by simple chlorinating agents that proceeds rapidly in water. The reaction is fast at acidic pH and tolerates alcohols, carboxylic acids, and even secondary amines in the substrates. It is applicable to the functionalization of primary amides, sulfonamides, and other N-functional groups that typically resist classical acylations and can be applied to late-stage functionalizations.

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Microwave-Assisted Synthesis of Acyclic Imides

Ölmez

2022

Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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Imides are an important class of compounds found in the structure of many biologically active and natural compounds. Imides are also important starting materials used in the synthesis of many heterocyclic compounds. Therefore, the synthesis of these compounds has attracted considerable attention and several innovative methods have been developed. Herein, the synthesis of acyclic imides has been reported from nitriles and carboxylic anhydrides in the presence of catalytic amounts of ptoluenesulfonic acid (PTSA) or H2SO4 under microwave irradiation. The reaction has proceeded in better yields with PTSA. When sulfuric acid was used, the product was obtained in lower yields since the degradation was increased. This new microwave-assisted method is compared with conventional heating, and the other methods, reported in the literature. The main advantages of this procedure are shorter reaction times, easier work-up, and good yields.

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A Novel One-Pot Synthesis of Unsymmetrical Acyclic Imides

Abstract: A new and convenient method was found for the one-pot synthesis of symmetrical and unsymmetrical linear imides by reaction of aliphatic and aromatic nitriles with acyclic carboxylic anhydrides in the presence of silica sulfuric acid as an active and recyclable reagent.

Cited by 4 publications

References 6 publications

DMAPO/Boc₂O‐Mediated One‐Pot Direct N‐Acylation of Less Nucleophilic N‐Heterocycles with Carboxylic Acids

DMAPO/Boc₂O‐Mediated One‐Pot Direct N‐Acylation of Less Nucleophilic N‐Heterocycles with Carboxylic Acids

Chemoselective Acylation of Primary Amines and Amides with Potassium Acyltrifluoroborates under Acidic Conditions

Microwave-Assisted Synthesis of Acyclic Imides

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A Novel One-Pot Synthesis of Unsymmetrical Acyclic Imides

Abstract: A new and convenient method was found for the one-pot synthesis of symmetrical and unsymmetrical linear imides by reaction of aliphatic and aromatic nitriles with acyclic carboxylic anhydrides in the presence of silica sulfuric acid as an active and recyclable reagent.

Cited by 4 publications

References 6 publications

DMAPO/Boc2O‐Mediated One‐Pot Direct N‐Acylation of Less Nucleophilic N‐Heterocycles with Carboxylic Acids

DMAPO/Boc2O‐Mediated One‐Pot Direct N‐Acylation of Less Nucleophilic N‐Heterocycles with Carboxylic Acids

Chemoselective Acylation of Primary Amines and Amides with Potassium Acyltrifluoroborates under Acidic Conditions

Microwave-Assisted Synthesis of Acyclic Imides

Contact Info

Product

Resources

About

DMAPO/Boc₂O‐Mediated One‐Pot Direct N‐Acylation of Less Nucleophilic N‐Heterocycles with Carboxylic Acids

DMAPO/Boc₂O‐Mediated One‐Pot Direct N‐Acylation of Less Nucleophilic N‐Heterocycles with Carboxylic Acids