A three-step strategy for the conversion of pyridines into benzonitriles

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

Published: March 7, 2025

Language: Английский

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Carbon–nitrogen transmutation in polycyclic arenol skeletons to access N-heteroarenes

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

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Skeletal Editing of Cyclic Molecules Using Nitrenes

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(21), P. 2656 - 2667

Published: July 16, 2024

Comprehensive Summary Nitrenes, as neutral monovalent nitrogen‐centered molecular species, can insert into various bond or remove nitrogen atoms from amines. Nitrene assisted single‐atom skeletal editing, discovered decades ago, provides an efficient approach for the precise alteration of cyclic skeletons. In this review, we briefly summarize early studies on editing frameworks involving nitrene and introduce several recent important advances systematically.

Language: Английский

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Carbene-Assisted Arene Ring-Opening

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(25), P. 16963 - 16970

Published: May 1, 2024

Despite the significant achievements in dearomatization and C–H functionalization of arenes, arene ring-opening remains a largely unmet challenge is underdeveloped due to high bond dissociation energy strong resonance stabilization inherent aromatic compounds. Herein, we demonstrate novel carbene assisted strategy for ring-opening. The understanding mechanism by our DFT calculations will stimulate wide application bulk chemicals synthesis value-added polyconjugated chain molecules. Various aryl azide derivatives now can be directly converted into valuable enynes, avoiding traditional including multistep unsaturated precursors, poor selectivity control, subsequent transition-metal catalyzed cross-coupling reactions. simple conditions required were demonstrated late-stage modification complex molecules fused ring This chemistry expands horizons provides pathway

Language: Английский

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Regioselective Pyridine to Benzene Edit Inspired by Water-Displacement

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

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