Improving the Efficiency of Sensitized Quinoxlin-2(1<i>H</i>)-ones via Pyrazolylation: Synthesis of Azetidines and Further Ring-Opening Reaction

Zhao, Caidan; Bai, Zhi-Qin; He, Jian; Liu, Qiang

doi:10.6023/cjoc202209028

Chinese Journal of Organic Chemistry

2022

DOI: 10.6023/cjoc202209028

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Improving the Efficiency of Sensitized Quinoxlin-2(1H)-ones via Pyrazolylation: Synthesis of Azetidines and Further Ring-Opening Reaction

Caidan Zhao¹,

Zhi-Qin Bai²,

Jian He³

et al.

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Cited by 3 publications

References 31 publications

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Navigating Visible‐Light‐Triggered (aza and thia) Paternò‐Büchi Reactions for the Synthesis of Heterocycles

Zhang,

Yang,

Zhang

et al. 2023

Adv Synth Catal

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Harnessing visible light to trigger (aza and thia) Paternò‐Büchi reaction injects new vitality into [2+2] photocyclization reaction and enable impressive reactivity modes. The popular (aza and thia) Paternò‐Büchi reaction is one of the most efficient ways to synthesize strained four‐membered heterocycles. Recently, visible‐light‐triggered (aza and thia) Paternò‐Büchi reactions have received considerable attentions as this strategy has overcome some long‐standing challenges, and remarkable achievements have been made within this field. Strained four‐membered heterocyclics with favorable properties provide a perfect combination of stable skeletons for pharmaceutical chemistry and raction intermediates for further transformation. In this review, we highlight the most recent advances in visible‐light‐triggered (aza and thia) Paternò‐Büchi reaction with an emphasis on reaction mechanism and applications. Organization of the review follows a subdivision according to reaction type and substrate classes.

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Navigating Visible‐Light‐Triggered (aza and thia) Paternò‐Büchi Reactions for the Synthesis of Heterocycles

Zhang,

Yang,

Zhang

et al. 2023

Adv Synth Catal

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An Organic EnT Photocatalyst 4CzMeBN and the Application in the Synthesis of cis‐Fused Azetidines

Feng,

Liu,

Xiang

et al. 2024

Chemistry A European J

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A powerful EnT photocatalyst 4CzMeBN has been developed and utilized in the synthesis of cis‐fused azetidines via dearomative [2+2] cycloaddition under visible light. The photocatalyst 4CzMeBN is a donor‐acceptor cyanoarene and features high triplet state energy and long lifetime of triplet state, which would be an alternative to widely used EnT photocatalyst Ir[dF(CF3)ppy]2(dtbbpy)PF6. The photochemical [2+2] cycloaddition provides a facile method to synthesize valuable dihydroisoquinolone‐fused azetidines with high efficiency.

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Recent advances in the synthesis of azetidines

Zadsirjan,

Soleimani

2025

Tetrahedron

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Improving the Efficiency of Sensitized Quinoxlin-2(1H)-ones via Pyrazolylation: Synthesis of Azetidines and Further Ring-Opening Reaction

Cited by 3 publications

References 31 publications

Navigating Visible‐Light‐Triggered (aza and thia) Paternò‐Büchi Reactions for the Synthesis of Heterocycles

Navigating Visible‐Light‐Triggered (aza and thia) Paternò‐Büchi Reactions for the Synthesis of Heterocycles

An Organic EnT Photocatalyst 4CzMeBN and the Application in the Synthesis of cis‐Fused Azetidines

Recent advances in the synthesis of azetidines

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