Nitrogen-to-Carbon Single Atom Point Mutation of Pyridine N-Oxides DOI Creative Commons
Nicholas Falcone, Sam He, John Hoskin

et al.

Published: Jan. 24, 2024

Single-atom editing has emerged as a powerful process for altering molecular structures with precision. Within this growing class of transformations, reactions that replace one atom another in heterocycles, while desirable, remain limited. We report the development transformation achieves an N-to-C swap pyridine N-oxides utilizing sulfoxide-derived anion carbon source. This ‘point mutation’ exhibits good functional group tolerance and replaces N-oxide moiety either unsubstituted, substituted, or isotopically labeled atoms single laboratory operation.

Language: Английский

Dearomatization of Pyridines: Photochemical Skeletal Enlargement for the Synthesis of 1,2-Diazepines DOI

Elise Boudry,

Flavien Bourdreux,

Jérôme Marrot

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(4), P. 2845 - 2854

Published: Jan. 18, 2024

In this report, we developed a unified and standardized one-pot sequence that converts pyridine derivatives into 1,2-diazepines by inserting nitrogen atom. This skeletal transformation capitalizes on the in situ generation of 1-aminopyridinium ylides, which rearrange under UV light irradiation. A thorough evaluation key parameters (wavelength, reaction conditions, activating agent) allowed us to elaborate simple, mild, user-friendly protocol. The model was extrapolated more than 40 examples, including drug derivatives, affording unique 7-membered structures. Mechanistic evidence supports transient presence diazanorcaradiene species. Finally, pertinent transformations products, ring contraction reactions form pyrazoles, were conducted paved way broad application

Language: Английский

Citations

34
Rational Molecular Editing: A New Paradigm in Drug Discovery DOI Creative Commons
Chunhua Ma, Craig W. Lindsley, Junbiao Chang

et al.

Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 67(14), P. 11459 - 11466

Published: June 21, 2024

ADVERTISEMENT RETURN TO ARTICLES ASAPPREVEditorialNEXTRational Molecular Editing: A New Paradigm in Drug DiscoveryChunhua MaChunhua MaState Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, NMPA for Research and Evaluation Innovative Drug, School Chemistry Chemical Engineering, Henan Normal University, Xinxiang, 453007, ChinaMore by Chunhua Mahttps://orcid.org/0000-0001-7613-6471, Craig W. Lindsley*Craig LindsleyVanderbilt University Medical Center, Franklin, Tennessee 37027, United States*E-mail: [email protected]More Lindsleyhttps://orcid.org/0000-0003-0168-1445, Junbiao Chang*Junbiao ChangCollege Chemistry, State Zhengzhou 450001, China*E-mail: Chang, Bin Yu*Bin YuCollege Yuhttps://orcid.org/0000-0002-7207-643XCite this: J. Med. Chem. 2024, XXXX, XXX, XXX-XXXPublication Date (Web):June 21, 2024Publication History Received13 June 2024Published online21 2024https://pubs.acs.org/doi/10.1021/acs.jmedchem.4c01347https://doi.org/10.1021/acs.jmedchem.4c01347editorialACS PublicationsPublished 2024 American Society. This publication is available under these Terms Use. Request reuse permissions free to access through this site. Learn MoreArticle Views-Altmetric-Citations-LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum full text article downloads since November 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated reflect usage leading up last few days.Citations number other articles citing article, calculated Crossref daily. Find more information about citation counts.The Altmetric Attention Score a quantitative measure attention that research has received online. Clicking on donut icon will load page at altmetric.com with additional details score social media presence given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InRedditEmail (2 MB) Get e-AlertscloseSUBJECTS:Drug discovery,Macrocyclization,Molecules,Pharmaceuticals,Scaffolds e-Alerts

Language: Английский

Citations

22
Photocatalytic furan-to-pyrrole conversion DOI

D.B. Kim,

Jaehyun You,

D. H. Lee

et al.

Science, Journal Year: 2024, Volume and Issue: 386(6717), P. 99 - 105

Published: Oct. 3, 2024

The identity of a heteroatom within an aromatic ring influences the chemical properties that heterocyclic compound. Systematically evaluating effect single atom, however, poses synthetic challenges, primarily as result thermodynamic mismatches in atomic exchange processes. We present photocatalytic strategy swaps oxygen atom furan with nitrogen group, directly converting into pyrrole analog intermolecular reaction. High compatibility was observed various derivatives and nucleophiles commonly used drug discovery, late-stage functionalization furnished otherwise difficult-to-access pyrroles from naturally occurring furans high molecular complexity. Mechanistic analysis suggested polarity inversion through electron transfer initiates redox-neutral processes at room temperature.

Language: Английский

Citations

16
Nitrogen atom insertion into arenols to access benzazepines DOI Creative Commons
Yi He, Juanjuan Wang,

Tongtong Zhu

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(7), P. 2612 - 2617

Published: Jan. 1, 2024

Advances in site-selective molecular editing have enabled structural modification on complex molecules.

Language: Английский

Citations

14
C(sp3)–C(sp3) bond formation through nitrogen deletion of secondary amines using O-diphenylphosphinylhydroxylamine DOI
Ting Guo, Jinghao Li,

Zhangkai Cui

et al.

Nature Synthesis, Journal Year: 2024, Volume and Issue: 3(7), P. 913 - 921

Published: June 7, 2024

Language: Английский

Citations

14
N‐(Sulfonio)Sulfilimine Reagents: Non‐Oxidizing Sources of Electrophilic Nitrogen Atom for Skeletal Editing DOI Creative Commons
Tobias Heilmann, Juan M. López‐Soria,

Johannes Ulbrich

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(25)

Published: April 16, 2024

The one-pot synthesis of λ

Language: Английский

Citations

12
Synthesis of Collidine from Dinitrogen via a Tungsten Nitride DOI

Lukas Eberle,

Joachim Ballmann

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(12), P. 7979 - 7984

Published: March 15, 2024

The synthesis of pyridines from dinitrogen in homogeneous solution is known to be challenging considering that an N2 cleavage step needs combined with two N–C coupling steps. Herein, a tungsten complex bearing tailor-made 2,2′-(tBu2As)2-substituted tolane ligand scaffold was shown split afford the corresponding nitride, which not case for (iPr2As)2-substituted derivative. former nitride then reacted 2,4,6-trimethylpyrylium triflate, led formation oxo complex, along collidine. Over course this reaction, O atom pyrylium starting material replaced N via hitherto unprecedented skeletal editing process.

Language: Английский

Citations

11
Reactivity of α-diazo sulfonium salts: rhodium-catalysed ring expansion of indenes to naphthalenes DOI Creative Commons

Sven Timmann,

Tun-Hui Wu,

Christopher Golz

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(16), P. 5938 - 5943

Published: Jan. 1, 2024

Cyclopropyl-substituted sulfonium salts are obtained by Rh-catalysed addition of α-diazo dibenzothiophenium to olefins. When indenes used as substrates, initially formed cyclopropyl rings open with concomitant elimination dibenzothiophene, enabling access 2-substituted naphthalenes.

Language: Английский

Citations

11
N-Oxide-to-Carbon Transmutations of Azaarene N-Oxides DOI
Nicholas Falcone, Sam He, John Hoskin

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4280 - 4285

Published: May 13, 2024

Reactions that change the identity of an atom within a ring system are emerging as valuable tools for site-selective editing molecular structures. Herein, we describe expansion underdeveloped transformation directly converts azaarene-derived N-oxides to all-carbon arenes. This transmutation exhibits good functional group tolerance and replaces N-oxide moiety with either unsubstituted, substituted, or isotopically labeled carbon atoms in single laboratory operation.

Language: Английский

Citations

11
Asymmetric dearomative single-atom skeletal editing of indoles and pyrroles DOI
Xiaolong Zhang, Qingmin Song, Shaopeng Liu

et al.

Nature Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 28, 2024

Language: Английский

Citations

11