☆ 4.6 Article

Nitrogen Heterocycle Synthesis through Hydride Abstraction of Acyclic Carbamates and Related Species: Scope, Mechanism, Stereoselectivity, and Product Conformation Studies

CHEMISTRY-A EUROPEAN JOURNAL (2023)

相关参考文献

注意：仅列出部分参考文献，下载原文获取全部文献信息。

Article Chemistry, Multidisciplinary

Mono- and Difluorinated Saturated Heterocyclic Amines for Drug Discovery: Systematic Study of Their Physicochemical Properties

Kostiantyn P. Melnykov et al.

Summary: A comprehensive study was conducted on the physicochemical properties of mono- and difluorinated azetidine, pyrrolidine, and piperidine derivatives. The basicity of the compounds was mainly determined by the number of fluorine atoms and their distance to the protonation center, while the conformational preferences significantly influenced the pK(a) and LogP values. High metabolic stability was observed for most compounds, except for the 3,3-difluoroazetidine derivative. The title compounds provide valuable building blocks for rational optimization studies in early drug discovery due to their unique properties.

CHEMISTRY-A EUROPEAN JOURNAL (2023)

添加到收藏夹

Article Chemistry, Multidisciplinary

Mechanism-Based Approach to Reagent Selection for Oxidative Carbon-Hydrogen Bond Cleavage Reactions

Jenna L. Miller et al.

Summary: This research investigates the influence of substrate features on the kinetics of oxidant-dependent hydride abstraction reactions, providing experimental data and computational studies to explain the results and mechanisms. Rigorous rate studies validate the predictive capacity of the calculations and guide the selection of optimal oxidants, which are also experimentally validated for reactivity predictions.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Kinetics-Based Approach to Developing Electrocatalytic Variants of Slow Oxidations: Application to Hydride Abstraction-Initiated Cyclization Reactions

Jean-Marc I. A. Lawrence et al.

Summary: This work presents a method for electrochemical oxoammonium ion regeneration by understanding the relationship between intermediate cation stability and reaction kinetics, which can expand the scope of electrocatalysis.

CHEMISTRY-A EUROPEAN JOURNAL (2022)

添加到收藏夹

Article Chemistry, Multidisciplinary

Alkynyl Prins carbocyclization cascades for the synthesis of linear-fused heterocyclic ring systems

Jackson J. Hernandez et al.

Summary: We report a Bronsted acid-catalyzed carbocyclization cascade that enables the synthesis of fused heterotricycles. The method exhibits high diastereoselectivity and produces versatile scaffolds with various functional groups for further derivatization.

CHEMICAL SCIENCE (2022)

添加到收藏夹

Review Chemistry, Multidisciplinary

Synthetic applications of hydride abstraction reactions by organic oxidants

Jenna L. Miller et al.

Summary: This review primarily focuses on the application of carbon-hydrogen bond functionalizations in organic synthesis, with a particular emphasis on the mechanism, reaction development, natural product synthesis applications, approaches to catalysis, and use in enantioselective processes for hydride abstractions by quinone, oxoammonium ion, and carbocation oxidants. In addition to the commonly used quinone, oxoammonium ion, and carbocation hydride-abstracting agents, the potential of weaker ketone and triaryl borane oxidants has also been studied.

CHEMICAL SOCIETY REVIEWS (2022)

添加到收藏夹

Article Chemistry, Organic

Characterization and Utilization of the Elusive α,β-Unsaturated N-Tosyliminium: the Synthesis of Highly Functionalizable Skipped Halo Enynes

Tapas R. Pradhan et al.

Summary: A formal haloalkynylation of allenamides has been described for the synthesis of highly stereo- and regioselective skipped halo enynes. The study demonstrates exclusive regioselectivity through the intermediary of a conjugated N-tosyliminium intermediate, with evidence validated by NMR and HRMS. Quantum mechanical computations reveal the importance of reactive intermediate geometry in controlling the regioselectivity of alkyne interception, providing divergent access to elusive unsaturated systems.

ORGANIC LETTERS (2021)

添加到收藏夹

Review Biochemistry & Molecular Biology

Recent advances in the development of covalent inhibitors

Hyunsoo Kim et al.

Summary: The use of covalent inhibitors in drug discovery has gained significant attention in the 2000s, with over 50 covalent drugs currently on the market and more in development. This review aims to provide an understanding of covalent inhibitors by exploring their characteristics, mechanisms, and potential applications, as well as introducing the latest covalent warheads for inhibitor development.

RSC MEDICINAL CHEMISTRY (2021)

添加到收藏夹

Review Chemistry, Medicinal

hERG toxicity assessment: Useful guidelines for drug design

Amanda Garrido et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2020)

添加到收藏夹

Article Chemistry, Multidisciplinary

Reference-free NOE NMR analysis

Martin R. M. Koos et al.

CHEMICAL SCIENCE (2020)

添加到收藏夹

Article Chemistry, Organic

Organocatalytic Asymmetric Dearomative Oxyalkylation of Indoles Enables Access to C2-Quaternary Indolin-3-ones

Xigong Liu et al.

ORGANIC LETTERS (2019)

添加到收藏夹

Review Chemistry, Medicinal

Pharmaceutical and medicinal significance of sulfur (SVI)-Containing motifs for drug discovery: A critical review

Chuang Zhao et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2019)

添加到收藏夹

Article Chemistry, Multidisciplinary

Predictive Model for Oxidative C-H Bond Functionalization Reactivity with 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

Cristian A. Morales-Rivera et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2017)

添加到收藏夹

Review Chemistry, Multidisciplinary

Scaffold Diversity from N-Acyliminium Ions

Peng Wu et al.

CHEMICAL REVIEWS (2017)

添加到收藏夹

Article Chemistry, Organic

Diastereoselectively Complementary C-H Functionalization Enables Access to Structurally and Stereochemically Diverse 2,6-Substituted Piperidines

Gang Wang et al.

ORGANIC LETTERS (2016)

添加到收藏夹

Article Chemistry, Multidisciplinary

Organocatalytic Enantioselective Oxidative C-H Alkenylation and Arylation of N-Carbamoyl Tetrahydropyridines and Tetrahydro-β-carbolines

Xigong Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

添加到收藏夹

Article Chemistry, Multidisciplinary

Acceleration of Acetal Hydrolysis by Remote Alkoxy Groups: Evidence for Electrostatic Effects on the Formation of Oxocarbenium Ions

Angie Garcia et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

添加到收藏夹

Article Chemistry, Organic

Influence of Alkoxy Groups on Rates of Acetal Hydrolysis and Tosylate Solvolysis: Electrostatic Stabilization of Developing Oxocarbenium Ion Intermediates and Neighboring-Group Participation To Form Oxoniunn Ions

Angie Garcia et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

添加到收藏夹

Article Chemistry, Organic

Toward a Unified Mechanism for Oxoammonium Salt-Mediated Oxidation Reactions: A Theoretical and Experimental Study Using a Hydride Transfer Model

Trevor A. Hamlin et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

添加到收藏夹

Article Chemistry, Organic

The Shono-type electroorganic oxidation of unfunctionalised amides. Carbon-carbon bond formation via electrogenerated N-acyliminium ions

Alan M. Jones et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2014)

添加到收藏夹

Article Chemistry, Medicinal

Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among US FDA Approved Pharmaceuticals

Edon Vitaku et al.

JOURNAL OF MEDICINAL CHEMISTRY (2014)

添加到收藏夹

Review Chemistry, Multidisciplinary

The diverse pharmacology and medicinal chemistry of phosphoramidates - a review

Fabricio M. Oliveira et al.

RSC ADVANCES (2014)

添加到收藏夹

Article Chemistry, Organic

Ruthenium Hydride/Bronsted Acid-Catalyzed Tandem Isomerization/N-Acyliminium Cyclization Sequence for the Synthesis of Tetrahydro-β-carbolines

Casper L. Hansen et al.

JOURNAL OF ORGANIC CHEMISTRY (2013)

添加到收藏夹

Article Chemistry, Organic

Ligand- and Base-Free Pd(II)-Catalyzed Controlled Switching between Oxidative Heck and Conjugate Addition Reactions

Sarah E. Walker et al.

ORGANIC LETTERS (2013)

添加到收藏夹

Article Chemistry, Medicinal

Substituted phenoxypropyl-(R)-2-methylpyrrolidine aminomethyl ketones as histamine-3 receptor inverse agonists

Allison L. Zulli et al.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2012)

添加到收藏夹

Article Chemistry, Multidisciplinary

Stereoselective piperidine synthesis through oxidative carbon-hydrogen bond functionalizations of enamides

Gediminas J. Brizgys et al.

CHEMICAL SCIENCE (2012)

添加到收藏夹

Review Chemistry, Organic

Strategies Based on Aryllithium and N-Acyliminium Ion Cyclizations for the Stereocontrolled Synthesis of Alkaloids and Related Systems

Unai Martinez-Estibalez et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2011)

添加到收藏夹

Review Chemistry, Multidisciplinary

Synthesis and Applications of tert-Butanesulfinamide

MaryAnn T. Robak et al.

CHEMICAL REVIEWS (2010)

添加到收藏夹

Article Chemistry, Multidisciplinary

Oxidative Carbocation Formation in Macrocycles: Synthesis of the Neopeltolide Macrocycle

Wangyang Tu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

添加到收藏夹

Article Chemistry, Organic

Cyclization Reactions through DDQ-Mediated Vinyl Oxazolidinone Oxidation

Lei Liu et al.

ORGANIC LETTERS (2009)

添加到收藏夹

Article Chemistry, Organic

Efficient Synthesis of 3-Alkoxy-4,4-difluoropiperidines

Riccardo Surmont et al.

SYNLETT (2009)

添加到收藏夹

Article Chemistry, Multidisciplinary

Total synthesis of theopederin D

Michael E. Green et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

添加到收藏夹

Article Chemistry, Multidisciplinary

Diastereoselective tetrahydropyrone synthesis through transition-metal-free oxidative carbon-hydrogen bond activation

Wangyang Tu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

添加到收藏夹

Article Chemistry, Organic

Gold-catalyzed synthesis of oxygen- and nitrogen-containing heterocycles from alkynyl ethers: Application to the total synthesis of andrachcinidine

Hyung Hoon Jung et al.

JOURNAL OF ORGANIC CHEMISTRY (2007)

添加到收藏夹

Article Chemistry, Multidisciplinary

Enantioselective Friedel-Crafts reaction of electron-rich alkenes catalyzed by chiral bronsted acid

Masahiro Terada et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

添加到收藏夹

Article Biochemical Research Methods

Revisiting the initial rate approximation in kinetic NOE measurements

Haitao Hu et al.

JOURNAL OF MAGNETIC RESONANCE (2006)

添加到收藏夹

Article Chemistry, Multidisciplinary

Alkyne hydrosilylation catalyzed by a cationic ruthenium complex: Efficient and general trans addition

BM Trost et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2005)

添加到收藏夹

Article Chemistry, Organic

PREPARATION OF 4-ACETYLAMINO-2, 2, 6, 6-TETRAMETHYLPIPERIDINE-1-OXOAMMONIUM TETRAFLUOROBORATE, AND THE OXIDATION OF GERANIOL TO GERANIAL (2,6-Octadienal, 3,7-dimethyl-, (2E)-)

James M. Bobbitt et al.

ORGANIC SYNTHESES (2005)

添加到收藏夹

Article Chemistry, Multidisciplinary

Ns strategies: a highly versatile synthetic method for amines

T Kan et al.

CHEMICAL COMMUNICATIONS (2004)

添加到收藏夹

Article Chemistry, Organic

Highly efficient stereoconservative amidation and deamidation of α-amino acids

DM Shendage et al.

ORGANIC LETTERS (2004)

添加到收藏夹

Review Chemistry, Multidisciplinary

Chiral heterocycles by iminium ion cyclization

J Royer et al.

CHEMICAL REVIEWS (2004)

添加到收藏夹

Article Chemistry, Multidisciplinary

Regiocontrolled Ru-catalyzed addition of carboxylic acids to alkynes: practical protocols for the synthesis of vinyl esters

LJ Goossen et al.

CHEMICAL COMMUNICATIONS (2003)

添加到收藏夹

Article Chemistry, Organic

Oxidative synthesis of cyclic acyl aminals through carbon-carbon σ-bond activation

DL Aubele et al.

ORGANIC LETTERS (2002)

添加到收藏夹

Article Chemistry, Organic

Silyl-substituted amino acids: New routes to the construction of selectively functionalized peptidomimetics

HZ Sun et al.

ORGANIC LETTERS (2002)

添加到收藏夹

© Peeref 2019-2024. All rights reserved.