ArticleChemistry (Weinheim an der Bergstrasse, Germany)2018
Synthesis of Benzannulated Medium-ring Lactams via a Tandem Oxidative Dearomatization-Ring Expansion Reaction.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Modular alkyl growth in amines via the selective insertion of alkynes into C-C bonds.Nature chemistry · 2025Article
- Lewis Acid-Catalyzed Domino Inverse Electron-Demand Diels-Alder/Thermal Ring Expansion Reaction for the Synthesis of Arene-Annulated Eight-Membered Nitrogen Heterocycles.Organic letters · 2025Article
- Medium-Sized Ring Expansion Strategies: Enhancing Small-Molecule Library Development.Molecules (Basel, Switzerland) · 2024Review
- Synthetic Potential of Regio- and Stereoselective Ring Expansion Reactions of Six-Membered Carbo- and Heterocyclic Ring Systems: A Review.International journal of molecular sciences · 2023Review
- A Lewis Acid-Promoted Michael Addition and Ring-Expansion Cascade for the Construction of Nitrogen-Containing Medium-Sized Rings.Molecules (Basel, Switzerland) · 2023Article
- Synthesis of medium-ring lactams and macrocyclic peptide mimeticsRSC chemical biology · 2022Article
- Evaluating the Viability of Successive Ring-Expansions Based on Amino Acid and Hydroxyacid Side-Chain Insertion.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- A happy medium: the synthesis of medicinally important medium-sized ringsChemical science · 2020Review
- A Scaffold-Diversity Synthesis of Biologically Intriguing Cyclic Sulfonamides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Synthesis of Benzo[b]azocin-2-ones by Aryl Amination and Ring-Expansion of α-(Iodophenyl)-β-oxoesters.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Synthesis of bicyclic ethers by a palladium-catalyzed oxidative cyclization-redox relay-π-allyl-Pd cyclization cascade reaction.Chemical communications (Cambridge, England) · 2019Article
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4 authors.
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Abstract
Medium-ring natural products exhibit diverse biological activities but such scaffolds are underrepresented in probe and drug discovery efforts due to the limitations of classical macrocyclization reactions. We report herein a tandem oxidative dearomatization-ring-expanding rearomatization (ODRE) reaction that generates benzannulated medium-ring lactams directly from simple bicyclic substrates. The reaction accommodates diverse aryl substrates (haloarenes, aryl ethers, aryl amides, heterocycles) and strategic incorporation of a bridgehead alcohol generates a versatile ketone moiety in the products amenable to downstream modifications. Cheminformatic analysis indicates that these medium rings access regions of chemical space that overlap with related natural products and are distinct from synthetic drugs, setting the stage for their use in discovery screening against novel biological targets.
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