Recent Advances on the Synthesis of Azepane‐Based Compounds

Chiacchio, Maria Assunta; Legnani, Laura; Chiacchio, Ugo; Iannazzo, Daniela

doi:10.1002/9781119757153.ch16

Cited by 5 publications

(2 citation statements)

References 70 publications

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“…Common strategies for the syntheses of substituted azepanes (Figure 1B) include various types of intramolecular cyclizations, [4+3] and related cycloadditions, expansion of strained ring intermediates, and ring-closing metathesis. 2 However, these de novo approaches largely require pre-installation of desired functionality and stereochemistry into the precursors and are not particularly modular; thus, there is intense interest in new methods for the synthesis of sevenmembered N-heterocycles that employ readily available precursors. Based on our group's long-standing interest in transition metal-catalyzed nitrene transfer (NT), we were intrigued by an underexplored strategy involving nitrene insertion into an aromatic ring to form the sevenmembered heterocycle.…”

Section: Introductionmentioning

confidence: 99%

Chemoselective silver-catalyzed nitrene transfer: Tunable syntheses of azepines and cyclic carbamimidates

Schroeder,

Lin,

Dai

et al. 2024

Preprint

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Azepines and their saturated azepane counterparts are important moieties in bioactive molecules but are underrepresented in current drug screening libraries. Herein, we report a mild and efficient azepine formation via silver-catalyzed dearomative nitrene transfer. A 2,2,2-trichloroethoxysulfonyl (Tces)-protected carbamimidate nitrene precursor, coupled with the appropriate ligand for silver, is essential for achieving the unexpected chemoselectivity between arene dearomatization and benzylic C(sp3)–H amination. Potential applications in the late-stage diversification of azepines to complex molecular scaffolds and diastereoselective hydrogenations to high Fsp3 azepanes are also highlighted.

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Section: Introductionmentioning

confidence: 99%

Chemoselective silver-catalyzed nitrene transfer: Tunable syntheses of azepines and cyclic carbamimidates

Schroeder,

Lin,

Dai

et al. 2024

Preprint

View full text Add to dashboard Cite

show abstract

“…1 Common strategies for the syntheses of substituted azepanes (Scheme 1B) include various types of intramolecular cyclizations, [4 + 3] and related cycloadditions, expansion of strained ring intermediates, and ring-closing metathesis. 2 However, these de novo approaches largely require preinstallation of desired functionality and stereochemistry into the precursors and are not particularly modular; thus, there is intense interest in new methods for the synthesis of sevenmembered N-heterocycles that employ readily available precursors. Based on our group's long-standing interest in transition metal-catalyzed nitrene transfer (NT), we were intrigued by an underexplored strategy involving nitrene insertion into an aromatic ring to form the seven-membered heterocycle.…”

Section: ■ Introductionmentioning

confidence: 99%

Chemoselective Silver-Catalyzed Nitrene Transfer: Tunable Syntheses of Azepines and Cyclic Carbamimidates

Schroeder,

Lin,

et al. 2024

J. Am. Chem. Soc.

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Azepines and their saturated azepane counterparts are important moieties in bioactive molecules but are under-represented in current drug screening libraries. Herein, we report a mild and efficient azepine formation via silver-catalyzed dearomative nitrene transfer. A 2,2,2-trichloroethoxysulfonyl (Tces)-protected carbamimidate nitrene precursor, coupled with the appropriate ligand for silver, is essential for achieving the unexpected chemoselectivity between arene dearomatization and benzylic C(sp 3 )−H amination. Potential applications in the late-stage diversification of azepines to complex molecular scaffolds and diastereoselective hydrogenations to sp 3 -rich derivatives are also highlighted.

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Seven-membered N-heterocycles as approved drugs and promising leads in medicinal chemistry as well as the metal-free domino access to their scaffolds

Leśniewska,

Przybylski

2024

European Journal of Medicinal Chemistry

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Recent Advances on the Synthesis of Azepane‐Based Compounds

Cited by 5 publications

References 70 publications

Chemoselective silver-catalyzed nitrene transfer: Tunable syntheses of azepines and cyclic carbamimidates

Chemoselective silver-catalyzed nitrene transfer: Tunable syntheses of azepines and cyclic carbamimidates

Chemoselective Silver-Catalyzed Nitrene Transfer: Tunable Syntheses of Azepines and Cyclic Carbamimidates

Seven-membered N-heterocycles as approved drugs and promising leads in medicinal chemistry as well as the metal-free domino access to their scaffolds

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