Uniting Amide Synthesis and Activation by PIII/PV–Catalyzed Serial Condensation: Three-Component Assembly of 2-Amidopyridines

JM Lipshultz, AT Radosevich - Journal of the American Chemical …, 2021 - ACS Publications
An organophosphorus (PIII/PV redox) catalyzed method for the three-component
condensation of amines, carboxylic acids, and pyridine N-oxides to generate 2 …

Mechanistic Approach Toward the C4‐Selective Amination of Pyridines via Nucleophilic Substitution of Hydrogen

H Choi, WS Ham, P van Bonn, J Zhang… - Angewandte Chemie …, 2024 - Wiley Online Library
The development of site‐selective functionalization of N‐heteroarenes is highly desirable in
streamlined synthesis. In this context, direct amination of pyridines stands as an important …

Synthesis of Quinoline-2-thiones by Selective Deoxygenative CH/CS Functionalization of Quinoline N-Oxides with Thiourea

DI Bugaenko, OA Tikhanova… - The Journal of Organic …, 2023 - ACS Publications
Quinoline-2-thiones valuable for synthetic and medicinal chemistry applications were
obtained with excellent regioselectivity employing a deoxygenative C–H functionalization of …

From Pyridine-N-oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy

DI Bugaenko, MA Yurovskaya, AV Karchava - Organic Letters, 2021 - ACS Publications
The reactions of pyridine-N-oxides with Ph3P under the developed conditions provide an
unprecedented route to (pyridine-2-yl) phosphonium salts. Upon activation with DABCO …

Direct C4 and C2 C–H Amination of Heteroarenes Using I (III) Reagents via a Cross Azine Coupling

BJ Motsch, AH Quach, JL Dutton… - The Journal of …, 2024 - ACS Publications
Aminated nitrogen heterocycles are valuable motifs across numerous chemical industries,
perhaps most notably in small molecule drug discovery. While numerous strategies for …

Beyond the Zincke Reaction: Modern Advancements in the Synthesis and Applications of N-Aryl Pyridinium Salts

BJ Motsch, SE Wengryniuk - Tetrahedron, 2024 - Elsevier
In this review, we highlight recent advances in the synthesis of N-aryl pyridinium salts, which
have moved beyond the classical Zincke SN Ar reaction to focus on strategies reliant on CN …

C2-selective, functional-group-divergent amination of pyrimidines by enthalpy-controlled nucleophilic functionalization

WS Ham, H Choi, J Zhang, D Kim… - Journal of the American …, 2022 - ACS Publications
Synthesis of heteroaryl amines has been an important topic in organic chemistry because of
their importance in small-molecule discovery. In particular, 2-aminopyrimidines represent a …

Synthesis of quinoxaline derivatives via aromatic nucleophilic substitution of hydrogen

A Zasada, J Brześkiewicz, D Antoniak… - Organic & …, 2023 - pubs.rsc.org
The electrophilic nature of quinoxaline has been explored in the vicarious nucleophilic
substitution (VNS) of hydrogen with various carbanions as nucleophiles in an attempt to …

A Simple Four‐Step Synthesis of the Potato Alkaloid Demissidine from the Common Sapogenin Tigogenin

A Baj, N Kaewnok, JA Rivas‐Loaiza… - … A European Journal, 2023 - Wiley Online Library
A simple synthesis method of solanidane alkaloids from common steroidal sapogenins was
developed. Previously described multi‐step transformations of tigogenin to demissidine (8 …

Six-membered ring systems: pyridines and benzo derivatives

JC Badenock - Progress in Heterocyclic Chemistry, 2021 - Elsevier
Pyridines and their benzo derivatives are versatile organic scaffolds celebrated for their
presence in a variety of agrochemicals, polymers, and pharmaceuticals. Accordingly, the …