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Synthetic Transformations of Amides and Esters in Organic Synthesis
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Synthetic Transformations of Amides and Esters in Organic Synthesis

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 August 2024) | Viewed by 13774

Special Issue Editors

Prof. Dr. Michal Szostak

E-Mail Website
Guest Editor
Department of Chemistry, Rutgers University, 73 Warren St., Newark, NJ 07102, USA
Interests: amide bonds; N-heterocyclic carbenes; C-N activation; C-H activation; C-O activation; lanthanides; cross-coupling; catalysis; reductions; reductive couplings; radical chemistry; synthetic methodology; natural products
Special Issues, Collections and Topics in MDPI journals
Dr. Guangchen Li

E-Mail Website
Guest Editor
Chemistry Department, Columbia University, New York, NY 10027, USA
Interests: amide and ester N–C/C–O activation; cross-coupling; NHC ligand development; kinetic studies of hydrogen atom transfer; hydrogen-atom-initiated radical cyclization
Special Issues, Collections and Topics in MDPI journals
Dr. Changan Wang

E-Mail Website
Guest Editor
College of Chemistry and Chemical Engineering, Taishan University, Taian 271000, China
Interests: amides cross-coupling reactions; transition-metal-NHC catalysis; heterogeneous catalysis; porous organic polymers

Special Issue Information

Dear Colleagues,

Amide and ester groups are among the most important functional groups in chemistry and biology. Both amide and ester functionalities play a key role in the synthesis of high-value molecules, such as pharmaceuticals and natural products. The synthetic transformations of amides and esters to other functional groups, such as esters, amides, ketones, alcohols, and amines, have been essential tools for chemists to construct and modify chemical architectures. However, the classical resonance of amide (nN → π*C=O) and ester (nO → π*C=O) bonds leads to the high stability of common amides and esters. Historically, this resonance represented a formidable challenge in synthetic transformations of amides and esters. It is important to mention that in the past ten years, transformations of amides have been enjoying a remarkable renaissance in cross-coupling reactions, enabled by the concept of ground-state destabilization of the amide bond by twisting and electronic activation. We are inviting you to contribute articles, perspectives and reviews to this Special Issue relating to the field of synthetic transformations of amides and esters in organic synthesis, as well as new synthetic methods and mechanistic studies in the field of carboxylic acid interconversion reactions.

Prof. Dr. Michal Szostak
Dr. Guangchen Li
Dr. Changan Wang
Guest Editors

Manuscript Submission Information

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Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • amides and esters
  • synthetic transformation
  • cross coupling reactions
  • C-N/C-O bond activation
  • cross-coupling
  • catalysis
  • carboxylic acid derivatives

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Published Papers (8 papers)

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Research

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9 pages, 1271 KiB  
Article
The Influence of Ligands on the Pd-Catalyzed Diarylation of Vinyl Esters
by Anna Brodzka, Dominik Koszelewski, Anna Trzeciak, Lena Ruzik, Malgorzata Grela and Ryszard Ostaszewski
Molecules 2024, 29(10), 2268; https://doi.org/10.3390/molecules29102268 - 11 May 2024
Viewed by 894
Abstract
The impact of ligands on the palladium-catalyzed 1,2-diarylation reaction course is presented. The application of Pd-dmpzc as a catalyst provides an efficient, chemoselective and sustainable protocol for the synthesis of valuable 1,2-diphenylethyl acetates. The reaction is conducted in water under mild conditions. Reaction [...] Read more.
The impact of ligands on the palladium-catalyzed 1,2-diarylation reaction course is presented. The application of Pd-dmpzc as a catalyst provides an efficient, chemoselective and sustainable protocol for the synthesis of valuable 1,2-diphenylethyl acetates. The reaction is conducted in water under mild conditions. Reaction products can be easily separated from the reaction mixture and catalyst by simple extraction. What is more, the rational choice of catalyst significantly reduces the leaching of the metal into the product and its contamination (0.1 ppm). Efficient phase separation and ultralow Pd leaching enable the reuse of the water medium containing the Pd-dmpzc catalyst several times without a significant loss of activity and with even higher selectivity (from 95% to 100% in the third cycle). The recyclability of both the catalyst and the reaction medium together with high chemoselectivity and low palladium leaching reduces the amount of waste and the cost of the process, exhibiting an example of a sustainable and green methodology. Full article
(This article belongs to the Special Issue Synthetic Transformations of Amides and Esters in Organic Synthesis)
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13 pages, 5364 KiB  
Article
Titanium Tetrachloride-Assisted Direct Esterification of Carboxylic Acids
by Palmira Alessia Cavallaro, Marzia De Santo, Marianna Greco, Rocco Marinaro, Emilia Lucia Belsito, Angelo Liguori and Antonella Leggio
Molecules 2024, 29(4), 777; https://doi.org/10.3390/molecules29040777 - 8 Feb 2024
Cited by 3 | Viewed by 2157
Abstract
Ester compounds, widely found in pharmaceutical and natural products, play a crucial role in organic synthesis, prompting the development of numerous methods for their synthesis. An important chemical approach in synthesizing esters from carboxylic acids involves the activation of the carboxyl function, requiring [...] Read more.
Ester compounds, widely found in pharmaceutical and natural products, play a crucial role in organic synthesis, prompting the development of numerous methods for their synthesis. An important chemical approach in synthesizing esters from carboxylic acids involves the activation of the carboxyl function, requiring the conversion of the hydroxyl group into a suitable leaving group. This paper presents the findings of our investigations into an efficient method for producing esters from carboxylic acids and alcohols, using the Lewis acid titanium tetrachloride. Titanium tetrachloride has proven highly effective as a coupling reagent for the one-pot formation of esters from carboxylic acids and alcohols operating under mild and neutral conditions. Notably, the reaction eliminates the need for bases, yielding carboxylic esters in high purity and yields. The method is efficient, even with long-chain carboxylic acids, and operates well with primary alcohols in dichloromethane. Steric hindrance, potentially present in carboxylic acids, has a moderate effect on the reaction. Alcohol substrates that easily form stable carbocations require, instead, the use of non-polar solvents like hexane for the reaction. Full article
(This article belongs to the Special Issue Synthetic Transformations of Amides and Esters in Organic Synthesis)
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8 pages, 780 KiB  
Communication
Borane-Pyridine: An Efficient Catalyst for Direct Amidation
by P. Veeraraghavan Ramachandran, Aman Singh, Harry Walker and Henry J. Hamann
Molecules 2024, 29(1), 268; https://doi.org/10.3390/molecules29010268 - 4 Jan 2024
Cited by 2 | Viewed by 2888
Abstract
Borane-pyridine acts as an efficient (5 mol%) liquid catalyst, providing improved solubility for the direct amidation of a wide range of aromatic and aliphatic carboxylic acids and amines to form secondary and tertiary carboxamides. Tolerance of potentially incompatible halo, nitro, and alkene functionalities [...] Read more.
Borane-pyridine acts as an efficient (5 mol%) liquid catalyst, providing improved solubility for the direct amidation of a wide range of aromatic and aliphatic carboxylic acids and amines to form secondary and tertiary carboxamides. Tolerance of potentially incompatible halo, nitro, and alkene functionalities has been demonstrated. Full article
(This article belongs to the Special Issue Synthetic Transformations of Amides and Esters in Organic Synthesis)
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Scheme 1

19 pages, 1890 KiB  
Article
Probing Reactivity with External Forces: The Case of Nitroacetamides in Water
by Giovanni La Penna and Fabrizio Machetti
Molecules 2024, 29(1), 9; https://doi.org/10.3390/molecules29010009 - 19 Dec 2023
Viewed by 886
Abstract
Many computational methods have been applied to interpret and predict changes in reactivity by slight modifications of a given molecular scaffold. We describe a novel and simple method based on approximate density-functional theory of valence electrons that can be applied within a large [...] Read more.
Many computational methods have been applied to interpret and predict changes in reactivity by slight modifications of a given molecular scaffold. We describe a novel and simple method based on approximate density-functional theory of valence electrons that can be applied within a large high-performance computational infrastructure to probe such changes using a statistical sample of molecular configurations, including the solvent. All the used computational tools are fully open-source. Following our previous application, we are able to explain the high acidity of C-H bond at α position in nitro compounds when the amide linkage an ammonium group is inserted into the α substituent. Full article
(This article belongs to the Special Issue Synthetic Transformations of Amides and Esters in Organic Synthesis)
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13 pages, 2378 KiB  
Article
Synthesis and Reactivity of Fluorinated Dithiocarboxylates to Prepare Thioamides—Effective Access to a 4-Styrenylthioamide-Cinchona Alkaloid Monomer
by Aimar Gonzalo-Barquero, Bénédicte Lepoittevin, Jacques Rouden and Jérôme Baudoux
Molecules 2023, 28(21), 7333; https://doi.org/10.3390/molecules28217333 - 30 Oct 2023
Cited by 1 | Viewed by 1435
Abstract
A simple and rapid access to fluorinated dithioesters was developed by a one-pot sequence corresponding to a Grignard reaction—Mitsunobu type substitution. These activated dithioesters have shown excellent reactivity in an aminolysis reaction from simple or more complex primary amines such as cinchona alkaloids. [...] Read more.
A simple and rapid access to fluorinated dithioesters was developed by a one-pot sequence corresponding to a Grignard reaction—Mitsunobu type substitution. These activated dithioesters have shown excellent reactivity in an aminolysis reaction from simple or more complex primary amines such as cinchona alkaloids. A stoichiometric amount of amine was sufficient to prepare various thioamides, including a 4-styrenylthioamide cinchonidine monomer, under environmentally friendly conditions, at room temperature, and in a very short time. Full article
(This article belongs to the Special Issue Synthetic Transformations of Amides and Esters in Organic Synthesis)
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12 pages, 4709 KiB  
Article
Domino Aldol-SNAr-Dehydration Sequence for [3+3] Annulations to Prepare Quinolin-2(1H)-ones and 1,8-Naphthyridin-2(1H)-ones
by Kwabena Fobi, Ebenezer Ametsetor and Richard A. Bunce
Molecules 2023, 28(15), 5856; https://doi.org/10.3390/molecules28155856 - 3 Aug 2023
Cited by 1 | Viewed by 1205
Abstract
A domino aldol-SNAr-dehydration [3+3] annulation strategy has been utilized to fuse six-membered cyclic amides onto aromatic substrates. 2-Arylacetamides have been reacted with 2-fluorobenzaldehyde derivatives activated toward SNAr reaction by an electron-withdrawing substituent (NO2, CN, CF3, [...] Read more.
A domino aldol-SNAr-dehydration [3+3] annulation strategy has been utilized to fuse six-membered cyclic amides onto aromatic substrates. 2-Arylacetamides have been reacted with 2-fluorobenzaldehyde derivatives activated toward SNAr reaction by an electron-withdrawing substituent (NO2, CN, CF3, CO2Me) at C5 to prepare 3,6-disubstituted quinolin-2(1H)-ones. Additionally, 3-substituted 1,8-naphthyridin-2(1H)-ones have been similarly derived from 2-fluoronicotinaldehyde. Fifteen examples are reported, and two possible mechanistic scenarios are presented and discussed. Full article
(This article belongs to the Special Issue Synthetic Transformations of Amides and Esters in Organic Synthesis)
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11 pages, 2165 KiB  
Article
Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone Derivatives
by Armands Maļeckis, Marija Cvetinska, Aleksandrs Puckins, Sergejs Osipovs, Jelizaveta Sirokova, Sergey Belyakov and Elena Kirilova
Molecules 2023, 28(13), 5171; https://doi.org/10.3390/molecules28135171 - 2 Jul 2023
Cited by 2 | Viewed by 1578
Abstract
In the present study, new fluorophores based on disubstituted benzanthrone derivatives were designed starting from 9-nitro-3-bromobenzanthrone with nucleophilic substitution of the bromine atom with some secondary cyclic amines. It has been found that this reaction is positively affected by the presence of a [...] Read more.
In the present study, new fluorophores based on disubstituted benzanthrone derivatives were designed starting from 9-nitro-3-bromobenzanthrone with nucleophilic substitution of the bromine atom with some secondary cyclic amines. It has been found that this reaction is positively affected by the presence of a nitro group in comparison with 3-bromobenzanthrone. The new compounds exhibit intense absorption and pronounced luminescent properties in various organic solvents. In this regard, their photophysical properties were evaluated with an experimental study of the solvatochromic behavior of the obtained compounds in various solvents. It has recently been found that the addition of an electron-withdrawing nitro group to the benzanthrone core increases its first- and second-order hyperpolarizability. Such dyes can be used in the fabrication of optical limiter devices. Therefore, the developed fluorescent molecules have a potential prospect for extensive application in optoelectronics. Full article
(This article belongs to the Special Issue Synthetic Transformations of Amides and Esters in Organic Synthesis)
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Review

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18 pages, 3595 KiB  
Review
Medium-Sized Ring Expansion Strategies: Enhancing Small-Molecule Library Development
by Hwiyeong Lee, Jonghoon Kim and Minseob Koh
Molecules 2024, 29(7), 1562; https://doi.org/10.3390/molecules29071562 - 31 Mar 2024
Cited by 3 | Viewed by 1706
Abstract
The construction of a small molecule library that includes compounds with medium-sized rings is increasingly essential in drug discovery. These compounds are essential for identifying novel therapeutic agents capable of targeting “undruggable” targets through high-throughput and high-content screening, given their structural complexity and [...] Read more.
The construction of a small molecule library that includes compounds with medium-sized rings is increasingly essential in drug discovery. These compounds are essential for identifying novel therapeutic agents capable of targeting “undruggable” targets through high-throughput and high-content screening, given their structural complexity and diversity. However, synthesizing medium-sized rings presents notable challenges, particularly with direct cyclization methods, due to issues such as transannular strain and reduced degrees of freedom. This review presents an overview of current strategies in synthesizing medium-sized rings, emphasizing innovative approaches like ring-expansion reactions. It highlights the challenges of synthesis and the potential of these compounds to diversify the chemical space for drug discovery, underscoring the importance of medium-sized rings in developing new bioactive compounds. Full article
(This article belongs to the Special Issue Synthetic Transformations of Amides and Esters in Organic Synthesis)
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