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

doi:10.6023/cjoc202209028

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (12): 4300-4314.DOI: 10.6023/cjoc202209028 Previous Articles Next Articles

Special Issue: 自由基化学专辑

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吡唑化提高喹喔啉酮敏化效率: 氮杂环丁烷的合成及进一步开环反应

赵成军, 白治琴, 何建, 刘强^*()

兰州大学化学化工学院功能有机高分子化学国家重点实验室兰州 730000

收稿日期:2022-09-21 修回日期:2022-10-21 发布日期:2022-11-21
通讯作者: 刘强
作者简介:
^†共同第一作者
基金资助:
国家自然科学基金(21871123)

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

Chengjun Zhao, Zhiqin Bai, Jian He, Qiang Liu()

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000

Received:2022-09-21 Revised:2022-10-21 Published:2022-11-21
Contact: Qiang Liu
About author:
^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21871123)

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Abstract

A mild approach to prepare functionalized azetidines by intermolecular aza Paternò-Büchi reaction using suitable auxochrome (pyrazole) to promote 3-pyrazolyl quinoxalin-2(1H)-ones into its excited state has been developed. Overall, pyrazolyl plays a key role in reducing the excited state energy of the triplet state of quinoxalinones, changing the redox potential and subsequent transformation as a good leaving group. The cross-dehydrogenative coupling (CDC)-amination, aza Paternò-Büchi reaction, and elimination reaction were also investigated.

Key words: visible light catalysis, aerobic oxidation, photocycloaddition, Paternò-Buchi reaction, energy transfer

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Chengjun Zhao, Zhiqin Bai, Jian He, Qiang Liu. Improving the Efficiency of Sensitized Quinoxlin-2(1H)-ones via Pyrazolylation: Synthesis of Azetidines and Further Ring-Opening Reaction[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4300-4314.

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Fig. & Tab. 7

Scheme 1. Strategies for the functionalization of quinoxalin-2(1H)-ones

Table 1. Scope of C-3 amination of quinoxalinonesa,b

Table 2. Substrate scope with respect to quinoxalinones derivativesa,b

Table 3. Scope alkenes of aza-Paternò-Büchi reactiona,b

Table 4. Scope of the difunctionalization of vinyl arenesa,b

Figure 1. (A) Normalized phosphorescence emission of 1a and 3a (λex=300 nm,150 μs delay) and (B) emission spectrum of PC (black line), luminescence quenching of 4CzIPN by 3a and 4a (λex=340 nm, 500 μs delay) in deoxygenated CPME at 77 K

Scheme 2. Proposed reaction mechanism for aza Paternò-Buchi reaction

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吡唑化提高喹喔啉酮敏化效率: 氮杂环丁烷的合成及进一步开环反应

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

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