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Towards More Practical Methods for the Chemical Synthesis of Thioamides Using Sulfuration Agents: A Decade Update

MOLECULES (2023)

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Article Biochemistry & Molecular Biology

Oxidative coupling of dibenzyl disulfide with amines catalyzed by quinoline-bromine complex: access to thioamides

Mehdi Rezapour et al.

Summary: The reaction of dibenzyl disulfide with various bromine complexes in the presence of DMSO as solvent can efficiently produce thioamides at 110 degrees C. Tertiary amines like pyridine and quinoline, which are included in the catalyst, generate bromine-addition complexes. This metal- and additive-free approach provides a simple and cost-effective method for synthesizing a variety of thioamides under favorable conditions.

MOLECULAR DIVERSITY (2023)

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Article Chemistry, Organic

Water Mediated Direct Thioamidation of Aldehydes at Room Temperature

Ankush Gupta et al.

Summary: A mild and greener method for thioamide synthesis has been developed, which involves a water-mediated reaction without the need for input energy, additives, or catalysts. This protocol offers the advantage of readily available starting materials and the use of different array amines, as well as a scalable method. It enables the synthesis of biologically active molecules such as thionicotinamide and thioisonicotinamide.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Organic

Ynamide-Mediated Thioamide and Primary Thioamide Syntheses

Changliu Wang et al.

Summary: This study describes an environmentally friendly synthesis of thioamides and primary thioamides using a simple and mild reaction conditions and readily available NaSH as the sulfur source. The reaction can tolerate a wide range of functional groups and maintains the stereochemical integrity of alpha-chiral monothiocarboxylic acids, offering a racemization-free strategy for peptide C-terminal modification. Additionally, this method can be used to prepare thioamide-modified drugs and backbone thiazolyl modified peptides.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Catalyst- and Solvent-Free Thioamidation of Aromatic Aldehydes through a Willgerodt-Kindler Reaction

Arun D. D. Kale et al.

Summary: A simple and efficient method for synthesizing thioamide derivatives has been developed using a one-pot multicomponent reaction. The method is catalyst- and solvent-free and can achieve high yields in a short reaction time.

CHEMISTRYSELECT (2022)

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Article Chemistry, Organic

Metal-Free Syntheses of α-Ketothioamide and α-Ketoamide Derivatives from Sulfoxonium Ylides

Trayambek Nath Chaubey et al.

Summary: An efficient method for the synthesis of alpha-ketothioamide and alpha-ketoamide derivatives has been developed using readily available sulfoxonium ylides. The reaction can be carried out without the use of additives or metals and yields good to excellent results. The reaction is scalable and can tolerate a range of functional groups with simple operational procedures.

ORGANIC LETTERS (2022)

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Article Chemistry, Organic

Csp3-H Bond Functionalization of α-Bromo Ketones for the Synthesis of α-Keto Thioamides Using Elemental Sulfur

Haiying Tian et al.

Summary: An efficient method for the metal- and additive-free synthesis of alpha-keto thioamides has been developed via sulfur oxidation of alpha-bromo ketones with amines. This environmentally friendly strategy allows for the synthesis of a wide range of alpha-keto thioamides with broad functional group tolerance.

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY (2022)

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Review Biochemistry & Molecular Biology

Sulfur incorporation into biomolecules: recent advances

Shramana Chatterjee et al.

Summary: This review provides an overview of the importance of sulfur in cellular metabolism and the various mechanisms by which sulfur is incorporated into biological molecules. It highlights recent advancements in sulfur transfer, iron-sulfur cluster destruction, and unconventional biosynthetic pathways.

CRITICAL REVIEWS IN BIOCHEMISTRY AND MOLECULAR BIOLOGY (2022)

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Article Biochemistry & Molecular Biology

Structural impact of thioamide incorporation into a β-hairpin

Kristen E. Fiore et al.

Summary: Thioamide substitution alters the characteristics of the amide bond and can have stabilizing, destabilizing, or neutral effects in proteins. Through experiments such as nuclear magnetic resonance, we investigated the impact of thioamides in a beta-hairpin scaffold and found that their stability depends on the position of incorporation.

RSC CHEMICAL BIOLOGY (2022)

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Article Chemistry, Organic

Thioamide synthesis via copper-catalyzed C-H activation of 1,2,3-thiadiazoles enabled by slow release and capture of thioketenes

Changhui Lu et al.

Summary: In this study, a simple and efficient Cu-catalyzed reaction for thioacylation of amines was developed. The method showed broad substrate scope and enabled late-stage thioamidation in various compounds.

ORGANIC CHEMISTRY FRONTIERS (2022)

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Article Chemistry, Organic

General Construction of Thioamides under Mild Conditions: A Stepwise Proton Transfer Process Mediated by EDTA

Hao Jin et al.

Summary: A new method for the one-pot synthesis of thioamides was developed in this study, which does not require transition metals or external oxidants. By using EDTA as a catalyst, alkyl and aryl thioamides with various functional groups can be obtained in moderate to good yields. The catalytic performance of EDTA is based on a stepwise, proton transfer process that lowers the associated barrier through discrete charge transfer.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Hydrogen Bond and Geometry Effects of Thioamide Backbone Modifications

Bryan J. Lampkin et al.

Summary: This study addresses the drawbacks in previous research that ignored the geometry dependence and local dielectric properties of thioamide hydrogen bonding. It identifies cases where thioamides may be either stronger or weaker hydrogen-bonding partners than amides.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Construction of Thioamide Peptide via Sulfur-Involved Amino Acids/Amino Aldehydes Coupling

Yanyan Liao et al.

Summary: A sulfur-involved ligation for thioamide quasi-peptides was developed via coupling of amino acids and amino aldehydes, with chelation of copper with imines for chiral activation and fixation being key to the transformation. Linear polysulfur was used to decrease the alkalinity of single sulfur anions, preventing racemization caused by interaction with sodium sulfide, resulting in successful synthesis of dipeptides, tripeptides, tetrapeptides, and drug-amino acid linkages.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

A chromatography-free and aqueous waste-free process for thioamide preparation with Lawesson's reagent

Ke Wu et al.

Summary: Ethanol was found to be effective in decomposing the byproduct of Lawesson's reagent, facilitating the preparation of thioamides. A convenient process using ethylene glycol instead of ethanol for post-reaction workup was successfully developed, reducing environmental pollution and offering the opportunity for large-scale thio-substitution reactions.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Metal-free three-component synthesis of thioamides from β-nitrostyrenes, amines and elemental sulfur

Ling Peng et al.

Summary: A metal-free C=C bond cleavage reaction of beta-nitrostyrenes in the presence of elemental sulfur and secondary amines/amides is reported, providing thioamides with good to excellent yields. The reaction features mild conditions and simple work-up procedure.

TETRAHEDRON LETTERS (2021)

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Article Chemistry, Organic

Copper-Catalyzed Decarboxylative Synthesis of α-Ketothioamides Using α,β-Unsaturated Arylcarboxylic Acids, Alicyclic Secondary Amines and Elemental Sulfur

Anjali Jaiswal et al.

Summary: An efficient and straightforward synthesis of alpha-ketothioamides has been achieved through in situ decarboxylative oxidative thioamidation using alpha,beta-unsaturated arylcarboxylic acids, alicyclic secondary amines, and elemental sulfur under solvent-free aerobic conditions.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Transition-Metal-Free, General Construction of Thioamides from Chlorohydrocarbon, Amide and Elemental Sulfur

Hao Jin et al.

Summary: A general method for one-pot synthesis of thioamides has been developed through a three-component reaction, avoiding residual transition metal and preventing the generation of C-N coupling by-product. This method offers high yields and tolerance towards various functional groups.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Efficient Synthesis of α-Ketothioamides From α-Nitroketones, Amines or DMF and Elemental Sulfur Under Oxidant-Free Conditions

Zhenlei Zhang et al.

Summary: A general, practical protocol has been developed for the synthesis of α-ketothioamides using sulfur and amines to denitrate alpha-nitroketones. The reaction operates under mild conditions without the need for metals, oxidants, or catalysts, and is especially useful for the synthesis of aliphatic α-ketothioamides, which are rarely reported.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

The catalytic role of elemental sulfur in the DMSO-promoted oxidative coupling of methylhetarenes with amines: synthesis of thioamides and bis-aza-heterocycles

Thi Thu Tram Nguyen et al.

Summary: Thioamides can be conveniently synthesized in good to excellent yields via DMSO-promoted oxidative coupling of methylhetarenes with amines in the presence of a near stoichiometric amount of sulfur (1.25 equiv.). Both aliphatic and aromatic amines were found to be competent substrates. When anilines o-substituted by cyclizable groups such as OH, NH2, NHPh, SH and CONH2 were used as amine substrates, the corresponding hybrid bis-aza-heterocycles were formed in high yields even with a sulfur loading as low as 0.5 equiv.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Article Chemistry, Organic

The thioamidation of gem-dibromoalkenes in an aqueous medium

Jigarkumar K. Vankar et al.

Summary: The direct integration of sulphur and amine groups with 1,1-dibromoalkenes for thioamide synthesis has been achieved in an aqueous medium. The green protocol enables greater selectivity with synthetic utility, leading to a wide range of thioamides in moderate to excellent yields using readily available starting materials, without the use of organic solvents, catalysts, or additives.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Solvent-driven C(sp3)-H thiocarbonylation of benzylamine derivatives under catalyst-free conditions

Jingwei Zhou et al.

Summary: A simple, practical, and environmentally friendly C(sp(3))-H thiocarbonylation method for benzylamine substrates has been developed without the need for a catalyst, enabling the facile synthesis of thioamides, with a diverse array of benzylamine derivatives being tolerated. The reaction mechanism involves specific solvents driving intermolecular hydrogen atom transfer (HAT) followed by single electron transfer (SET) to catalyze C-S bond formation and intramolecular HAT to establish the C=S bond.

GREEN CHEMISTRY (2021)

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Article Chemistry, Organic

NaOTs-promoted transition metal-free C-N bond cleavage to form C-X (X = N, O, S) bonds

Yuqi Zhang et al.

Summary: A multifunctional transformation of amide C-N bond cleavage is reported, applicable to benzamide, thioamide, alcohols, and mercaptan under similar reaction conditions catalyzed by NaOTs. The catalyst NaOTs can be recycled and reused for up to three cycles without significant loss in catalytic activity, also catalyzing gram-grade reactions. This study provides a novel solution with mild conditions and a simple procedure for transformation of multiple amides.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Mixed bases mediated synthesis of thioamides in water

Jiao Li et al.

JOURNAL OF SULFUR CHEMISTRY (2020)

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Article Chemistry, Organic

Thioamidation of Arylpropyne Derivatives with Sulfur and Formamides for the Synthesis of Aryl Propanethioamides

Hong-Hui Xu et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Mild and Chemoselective Thioacylation of Amines Enabled by the Nucleophilic Activation of Elemental Sulfur

Masato Saito et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Medicinal

Amide Bond Bioisosteres: Strategies, Synthesis, and Successes

Shikha Kumari et al.

JOURNAL OF MEDICINAL CHEMISTRY (2020)

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Article Chemistry, Organic

Synthesis of Substituted Thioamides from gem-Dibromoalkenes and Sodiumsulfide

Ashok K. Morri et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Organic

Metal-Free C-N or C-C Bond Cleavages of α-Azido Ketones: An Oxidative-Amidation Strategy for the Synthesis of α-Ketothioamides and Amides

Pei Yu et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Ynamide-Mediated Thiopeptide Synthesis

Jinhua Yang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Organic

Synthesis of α-Keto Thioamides by Metal-Free C=C Bond Cleavage in Enaminones Using Elemental Sulfur

Lu Gan et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

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Review Biochemistry & Molecular Biology

Biosynthesis and Chemical Applications of Thioamides

Nilkamal Mahanta et al.

ACS CHEMICAL BIOLOGY (2019)

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Article Chemistry, Applied

Synthesis of Phosphoryl Thioamides via Three-Component Reaction of Phosphinic Chlorides with Amines and Sulfur

Mikhail Kozlov et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

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Functionalization of activated methylene C-H bonds with nitroarenes and sulfur for the synthesis of thioamides

Nhan T. Do et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

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Microwave-assisted iodine-catalyzed oxidative coupling of dibenzyl(difurfuryl)disulfides with amines: a rapid and efficient protocol for thioamides

Jinyang Chen et al.

RSC ADVANCES (2019)

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Ionic liquid catalysed aerobic oxidative amidation and thioamidation of benzylic amines under neat conditions

Abhisek Joshi et al.

GREEN CHEMISTRY (2019)

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Enzymatic Thioamide Formation in a Bacterial Antimetabolite Pathway

Agnieszka Litomska et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Carbon nitride creates thioamides in high yields by the photocatalytic Kindler reaction

B. Kurpil et al.

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Bioinformatic Expansion and Discovery of Thiopeptide Antibiotics

Christopher J. Schwalen et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Transition-Metal-Free Cleavage of C-C Triple Bonds in Aromatic Alkynes with S-8 and Amides Leading to Aryl Thioamides

Kai Xu et al.

ORGANIC LETTERS (2018)

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A efficient protocol for the synthesis of thioamides in [DBUH][OAc] at room temperature

Xian-Ting Cao et al.

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K2S2O8-Promoted Aryl Thioamides Synthesis from Aryl Aldehydes Using Thiourea as the Sulfur Source

Yongjun Bian et al.

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Base-Controlled Three Component Reactions of Amines, Elemental Sulfur, and Styrenes: Synthesis of Thioamides under Metal-Free Conditions

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Aqueous MCRs of quaternary ammoniums, N-substituted formamides and sodium disulfide towards aryl thioamides

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Recent Advances in Organic Reactions Involving Elemental Sulfur

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Aqueous Compatible Protocol to Both Alkyl and Aryl Thioamide Synthesis

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Iodine-Promoted Synthesis of Thioamides from 1,2-Dibenzylsulfane and Difurfuryl Disulfide

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S8-Mediated One-Pot Synthesis of Thioamides from Benzyl Chlorides and Amines

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Dimethylamine as the key intermediate generated in situ from dimethylformamide (DMF) for the synthesis of thioamides

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Catalyst-Free, Atom-Economic, Multicomponent Polymerizations of Aromatic Diynes, Elemental Sulfur, and Aliphatic Diamines toward Luminescent Polythioamides

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Thiol as a Synthon for Preparing Thiocarbonyl: Aerobic Oxidation of Thiols for the Synthesis of Thioamides

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Room-Temperature Ligand-Free Pd/C-Catalyzed C-S Bond Formation: Synthesis of 2-Substituted Benzothiazoles

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Synthesis of thioamides via one-pot A3-coupling of alkynyl bromides, amines, and sodium sulfide

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Copper(II)-Catalyzed Reactions of Dimethylformamide with Phenylacetonitrile and Sulfur to Form N,N-Dimethylthioamides

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Microwave-assisted synthesis of thioamides with elemental sulfur

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Efficient and Selective Multicomponent Oxidative Coupling of Two Different Aliphatic Primary Amines into Thioamides by Elemental Sulfur

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