Carbon atom insertion into N-heterocyclic carbenes to yield 3,4-dihydroquinoxalin-2(1H)-ones DOI Creative Commons
Lamb Justin,

Futa Koyama,

Noriyuki Suzuki

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(2), P. 277 - 283

Published: Nov. 10, 2023

A molecular editing strategy to construct quinoxalinones from chromones and benzimidazolylidene N -heterocyclic carbenes (NHCs) was developed. The C2 atoms of the were incorporated into via ring expansion NHCs.

Language: Английский

Skeletal editing of pyridines through atom-pair swap from CN to CC DOI Creative Commons
Qiang Cheng,

Debkanta Bhattacharya,

Malte Haring

et al.

Nature Chemistry, Journal Year: 2024, Volume and Issue: 16(5), P. 741 - 748

Published: Jan. 18, 2024

Abstract Skeletal editing is a straightforward synthetic strategy for precise substitution or rearrangement of atoms in core ring structures complex molecules; it enables quick diversification compounds that not possible by applying peripheral strategies. Previously reported skeletal common arenes mainly relies on carbene- nitrene-type insertion reactions rearrangements. Although powerful, efficient and applicable to late-stage heteroarene structure modification, these strategies cannot be used pyridines. Here we report the direct pyridines through atom-pair swap from CN CC generate benzenes naphthalenes modular fashion. Specifically, use sequential dearomatization, cycloaddition rearomatizing retrocycloaddition one-pot sequence transform parent into bearing diversified substituents at specific sites, as defined reaction components. Applications pyridine cores several drugs are demonstrated.

Language: Английский

Citations

56
Ring expansion of indene by photoredox-enabled functionalized carbon-atom insertion DOI
Fu‐Peng Wu, Chetan C. Chintawar, Rémy F. Lalisse

et al.

Nature Catalysis, Journal Year: 2024, Volume and Issue: 7(3), P. 242 - 251

Published: Jan. 9, 2024

Language: Английский

Citations

37
Synthesis of benzenes from pyridines via N to C switch DOI Creative Commons

Aífe Conboy,

Michael F. Greaney

Chem, Journal Year: 2024, Volume and Issue: 10(6), P. 1940 - 1949

Published: June 1, 2024

The skeletal editing of heteroarenes introduces new disconnections to the chemistry lexicon, enabling interconversion ring systems via selective breaking/re-making carbon framework. We describe one-pot transformation pyridines into benzene derivatives, using a nucleophilic addition ring-opening/ring-closing (ANRORC) process with soft nucleophiles such as malonate. Triflic anhydride activates pyridine ANRORC synthesis an isolable amine intermediate, which aromatizes on simple heating. reaction has been exemplified room temperature protocol, along direct syntheses drug-like, tertiary-alkylated, and isotopically labeled benzoates.

Language: Английский

Citations

12
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
Precision single-atom editing: new frontiers in nitrogen insertion and substitution for the generation of N-heterocycles DOI
Xue Li, Jia Xu, Zhigang Xu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 4041 - 4053

Published: Jan. 1, 2024

This paper primarily focuses on the editing of nitrogen atoms, encompassing insertion N, substitution C with and utilization 15 N in place 14 for construction N-heterocycles.

Language: Английский

Citations

10
Synthesis of naphthalene derivatives via nitrogen-to-carbon transmutation of isoquinolines DOI Creative Commons

Tongtong Zhu,

Xiang Cui, Wenjun Ma

et al.

Science Advances, Journal Year: 2025, Volume and Issue: 11(5)

Published: Jan. 29, 2025

Heteroarene skeletal editing is gaining popularity in synthetic chemistry. Transmuting single atoms generates molecules that have distinctly varied properties, thereby fostering potent molecular exchanges can be extensively used to synthesize functional molecules. Herein, we present a convenient protocol for nitrogen-carbon single-atom transmutations isoquinolines, which inspired by the Wittig reaction and enables easy access substituted naphthalene derivatives. The uses an inexpensive commercially available phosphonium ylide as carbon source furnish wide range of naphthalenes. key success this transformation formation triene intermediate through ring opening, undergoes 6π-electrocyclization elimination processes afford product. Furthermore, strategy facile synthesis 13 C-labeled naphthalenes using CH 3 PPh I commercial C facilitates modifying directing group C─H functionalization.

Language: Английский

Citations

1
A three-step strategy for the conversion of pyridines into benzonitriles DOI Creative Commons

Reyhan Güdük,

Niklas Kehl,

Chiara Stavagna

et al.

Nature Synthesis, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

Language: Английский

Citations

1
Carbon–nitrogen transmutation in polycyclic arenol skeletons to access N-heteroarenes DOI Creative Commons
Hong Lu, Yu Zhang, Xiuhong Wang

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: May 4, 2024

Abstract Developing skeletal editing tools is not a trivial task, and realizing the corresponding single-atom transmutation in ring system without altering size even more challenging. Here, we introduce strategy that enables polycyclic arenols, highly prevalent motif bioactive molecules, to be readily converted into N -heteroarenes through carbon–nitrogen transmutation. The reaction features selective nitrogen insertion C–C bond of arenol frameworks by azidative dearomatization aryl migration, followed ring-opening, ring-closing (ANRORC) achieve carbon-to-nitrogen aromatic framework arenol. Using widely available arenols as -heteroarene precursors, this alternative approach allows streamlined assembly complex heteroaromatics with broad functional group tolerance. Finally, pertinent transformations products, including synthesis biheteroarene skeletons, were conducted exhibited significant potential materials chemistry.

Language: Английский

Citations

8
Regioselective Pyridine to Benzene Edit Inspired by Water-Displacement DOI
Benjamin R. Boswell, Zhen‐Sheng Zhao, Ryan L. Gonciarz

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(29), P. 19660 - 19666

Published: July 12, 2024

Late-stage derivatization of drug-like functional groups can accelerate drug discovery efforts by swiftly exchanging hydrogen-bond donors with acceptors, or modulating key physicochemical properties like logP, solubility, polar surface area. A proven strategy to improve ligand potency is extend the displace water molecules that are mediating interactions a receptor. Inspired this application, we developed method regioselectively transmute nitrogen atom from pyridine into carbon bearing an ester, flexible group handle. We applied variety substituted pyridines, as well late-stage transformation FDA-approved drugs.

Language: Английский

Citations

7
Nitrogen-to-functionalized carbon atom transmutation of pyridine DOI Creative Commons
Fu‐Peng Wu,

Madina Lenz,

Adhya Suresh

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(37), P. 15205 - 15211

Published: Jan. 1, 2024

The targeted and selective replacement of a single atom in an aromatic system represents powerful strategy for the rapid interconversion molecular scaffolds. Herein, we report pyridine-to-benzene transformation

Language: Английский

Citations

5