4.8 Article

Esterification of Thioamides via Selective N-C(S) Cleavage under Mild Conditions

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

Construction of Thioamide Peptides from Chiral Amino Acids

Yanyan Liao et al.

Summary: Thioamide peptides were synthesized in a one-pot process by linking natural amino acids in the presence of thiolphosphonate and trichlorosilane, with minimal racemization. Experimental and computational studies showed that trichlorosilane enables the activation of carboxylic acids and coupling with thiolphosphonate to obtain the intermediate S-acyl dithiophosphate. Silyl-activated quadrangular metathesis transition states resulted in the formation of thioamide peptides.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2023)

Article Chemistry, Multidisciplinary

Chemoselective Transamidation of Thioamides by Transition-Metal-Free N-C(S) Transacylation

Guangchen Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Organic

An efficient and straightforward approach for accessing thionoesters via palladium-catalyzed C-N cleavage of thioamides

Yinbo Liu et al.

Summary: We report a new method for the efficient formation of thionoesters through the coupling of activated thioamides with alcohols via a palladium-catalyzed C-N cleavage strategy. This methodology achieves moderate to good yields and exhibits a broad substrate scope, with alkyl/aryl alcohols being well tolerated. It provides a simple and mild approach for the synthesis of sulfur-containing compounds.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Organic

Transamidation of thioamides with nucleophilic amines: thioamide N-C(S) activation by ground-state-destabilization

Jin Zhang et al.

Summary: This article presents a strategy for activation of N-C(S) thioamide bonds by ground-state-destabilization, which can be used in transamidation reactions and modify the properties of thioamide isosteres in organic synthesis. It is expected to find broad applications in various facets of chemical science, including metal-free, metal-catalyzed, and metal-promoted reaction pathways.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

Article Chemistry, Organic

Transamidation of N-Benzyl-N-Boc-amides under Transition Metal-Free and Base-Free Conditions

Danfeng Ye et al.

Summary: The new protocol allows for the transamidation of N-benzyl-N-Boc-amides under transition metal-free and base-free conditions, resulting in a diverse array of substituted amides in good yields. Notably, the reaction preserves enantiopurity with respect to chiral amino-acid-derived nucleophiles. The method has been successfully applied in the synthesis of pro-drugs and the antidepressant moclobemide.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Kinetically Controlled, Highly Chemoselective Acylation of Functionalized Grignard Reagents with Amides by N-C Cleavage

Guangchen Li et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

Article Chemistry, Multidisciplinary

Economic Sulfur Conversion to Functional Polythioamides through Catalyst-Free Multicomponent Polymerizations of Sulfur, Acids, and Amines

Wenxia Cao et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Chemistry, Multidisciplinary

Highly Chemoselective, Transition-Metal-Free Transamidation of Unactivated Amides and Direct Amidation of Alkyl Esters by N-C/O-C Cleavage

Guangchen Li et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

Article Chemistry, Multidisciplinary

Enantioselective C(sp3)-H Amidation of Thioamides Catalyzed by a CobaltIII/Chiral Carboxylic Acid Hybrid System

Seiya Fukagawa et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Biochemistry & Molecular Biology

Biosynthesis and Chemical Applications of Thioamides

Nilkamal Mahanta et al.

ACS CHEMICAL BIOLOGY (2019)

Article Biochemistry & Molecular Biology

Thioamide substitution to probe the hydroxyproline recognition of VHL ligands

Pedro Soares et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2018)

Article Chemistry, Multidisciplinary

Albusnodin: an acetylated lasso peptide from Streptomyces albus

Chuhan Zong et al.

CHEMICAL COMMUNICATIONS (2018)

Article Chemistry, Multidisciplinary

Reversible Twisting of Primary Amides via Ground State N-C(O) Destabilization: Highly Twisted Rotationally Inverted Acyclic Amides

Guangrong Meng et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Review Biochemistry & Molecular Biology

Amide Bond Activation of Biological Molecules

Sriram Mahesh et al.

MOLECULES (2018)

Article Multidisciplinary Sciences

Highly selective transition-metal-free transamidation of amides and amidation of esters at room temperature

Guangchen Li et al.

NATURE COMMUNICATIONS (2018)

Article Chemistry, Physical

Breaking Amides using Nickel Catalysis

Jacob E. Dander et al.

ACS CATALYSIS (2017)

Article Chemistry, Multidisciplinary

Nickel-Catalyzed Esterification of Aliphatic Amides

Liana Hie et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

Article Chemistry, Multidisciplinary

Fmoc solid-phase synthesis of C-terminal modified peptides by formation of a backbone cyclic urethane moiety

Hader E. Elashal et al.

CHEMICAL COMMUNICATIONS (2016)

Article Chemistry, Multidisciplinary

Structures of Highly Twisted Amides Relevant to Amide N-C Cross-Coupling: Evidence for Ground-State Amide Destabilization

Vittorio Pace et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

Article Chemistry, Medicinal

A Survey of the Role of Noncovalent Sulfur Interactions in Drug Design

Brett R. Beno et al.

JOURNAL OF MEDICINAL CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

n→π* Interactions of Amides and Thioamides: Implications for Protein Stability

Robert W. Newberry et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2013)

Article Chemistry, Organic

Reliable Determination of Amidicity in Acyclic Amides and Lactams

Stephen A. Glover et al.

JOURNAL OF ORGANIC CHEMISTRY (2012)

Review Chemistry, Organic

Decarboxylative Carbon-Carbon Bond-Forming Transformations of (Hetero)aromatic Carboxylic Acids

Josep Cornella et al.

SYNTHESIS-STUTTGART (2012)

Review Biochemistry & Molecular Biology

An Evaluation of Peptide-Bond Isosteres

Amit Choudhary et al.

CHEMBIOCHEM (2011)

Review Chemistry, Multidisciplinary

Peptide Coupling Reagents, More than a Letter Soup

Ayman El-Faham et al.

CHEMICAL REVIEWS (2011)

Review Chemistry, Multidisciplinary

Decarboxylative coupling reactions: a modern strategy for C-C-bond formation

Nuria Rodriguez et al.

CHEMICAL SOCIETY REVIEWS (2011)

Article Chemistry, Inorganic & Nuclear

Metal ion directed self-assembly of sensors for ions, molecules and biomolecules

Jim A. Thomas

DALTON TRANSACTIONS (2011)

Review Multidisciplinary Sciences

Rethinking amide bond synthesis

Vijaya R. Pattabiraman et al.

NATURE (2011)

Article Chemistry, Multidisciplinary

Amide resonance correlates with a breadth of C-N rotation barriers

Carl R. Kemnitz et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Multidisciplinary Sciences

Synthesis and structural analysis of 2-quinuclidonium tetrafluoroborate

Kousuke Tani et al.

NATURE (2006)

Article Chemistry, Multidisciplinary

Water-promoted hydrolysis of a highly twisted amide: Rate acceleration caused by the twist of the amide bond

JI Mujika et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

Article Chemistry, Multidisciplinary

A fast photoswitch for minimally perturbed peptides:: Investigation of the trans→cis photoisomerization of N-methylthioacetamide

J Helbing et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2004)

Article Chemistry, Organic

Thionation with the reagent combination of phosphorus pentasulfide and hexamethyldisiloxane

TJ Curphey

JOURNAL OF ORGANIC CHEMISTRY (2002)

Article Chemistry, Multidisciplinary

Solvent effects on the thioamide rotational barrier: An experimental and theoretical study

KB Wiberg et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)