Synthesis of Curved Polycyclic Arenes Embedded with Oxepine and Thiepine Using Ring Expansion Strategy

Zhang, Sheng; Matsuyama, Hidenori; Nakamura, Itaru; Terada, Masahiro; Jin, Tienan

doi:10.1021/acs.orglett.3c01730

Cited by 3 publications

(2 citation statements)

References 33 publications

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“…We envisioned that the generation of a carbon centered cation on the methyl-group might lead to a rapid Friedel–Crafts type ring expansion (see Table ). − A similar mechanism was previously proposed by Huang et al in their metathesis of para -quinone methides with 3-diazo oxindoles . Indeed, we observed that upon treatment of starting material 1ab with AgBF 4 as a halogen scavenger, the desired 3-substituted quinolinone 2a could be obtained in excellent yield (Scheme ).…”

supporting

confidence: 80%

Regiodivergent Ring-Expansion of Oxindoles to Quinolinones

Schmitt,

Martymianov,

Green

et al. 2024

J. Am. Chem. Soc.

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The development of divergent methods to expedite structure−activity relationship studies is crucial to streamline discovery processes. We developed a rare example of regiodivergent ring expansion to access two regioisomers from a common starting material. To enable this regiodivergence, we identified two distinct reaction conditions for transforming oxindoles into quinolinone isomers. The presented methods proved to be compatible with a variety of functional groups, which enabled the latestage diversification of bioactive oxindoles as well as facilitated the synthesis of quinolinone drugs and their derivatives.

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supporting

confidence: 80%

Regiodivergent Ring-Expansion of Oxindoles to Quinolinones

Schmitt,

Martymianov,

Green

et al. 2024

J. Am. Chem. Soc.

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“…18 We assumed that if an intramolecular TORE reaction occurs with o ─ biphenyl─ linked methylenexanthene 6a under the appropriate oxidation conditions, desired heptagon─ fused structure dibenzo[b,f]phenanthro [9,10─ d]oxepine (DBPO) (7a) would be constructed (Figure 13). 8 Unfortunately, initial experiments using our previous oxidation systems, 6 such as CuCl/TBPB/TFA and DDQ/TFA, ( 54 ) J. Synth. Org.…”

Section: ． Intermolecular Ring Expansion Of Five ─ To Six ─ Memberedmentioning

confidence: 99%

Synthesis of Structurally Diverse Polycyclic Arenes Using Tandem Oxidative Ring Expansion Strategy

Jin,

Terada

2023

J. Synth. Org. Chem. Jpn.

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The impressive structural diversity of polycyclic arenes (PCAs) comprised of pentagon, hexagon, heptagon, and octagon rings has continued to drum up interest in the elds of synthetic chemistry and materials science owing to their tunable electronic properties in relation to their unique planar, twisted, and curved π ─ surface conformations. Although an array of synthetic strategies have been developed to construct both known and new PCA scaffolds in the past decades, exible and expedient strategies for creating PCAs with differently sized rings embedded are rare. We describe herein our recent studies on the tandem oxidative ring expansion (TORE) strategy for the construction of structurally diverse PCAs involving intra─ and intermolecular TORE reactions for hexagon─ embedded PCAs, and intramolecular TORE reactions for O─ or S─ incorporated hepta-gon─ embedded PCAs and octagon─ embedded PCAs.

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Seven-membered ring systems

Aitken

2024

Progress in Heterocyclic Chemistry

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Synthesis of Curved Polycyclic Arenes Embedded with Oxepine and Thiepine Using Ring Expansion Strategy

Cited by 3 publications

References 33 publications

Regiodivergent Ring-Expansion of Oxindoles to Quinolinones

Regiodivergent Ring-Expansion of Oxindoles to Quinolinones

Synthesis of Structurally Diverse Polycyclic Arenes Using Tandem Oxidative Ring Expansion Strategy

Seven-membered ring systems

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