异吲哚啉-1-酮和异喹啉-1-酮作为核心骨架广泛存在天然产物和重要的药物分子结构中，从绿色化学和分子多样性角度出发，开展构建此类结构的温和、通用方法尤为重要。众所周知，合成金属卟啉作为仿酶催化剂在苄型C-H键的羟基化反应中广泛应用，同样，N-羟基邻苯二甲酰亚胺 (NHPI)能有有效介导氧气的活化也广泛应用于各种有机物的氧化，在实验室前期工作基础上，基于上述思路，本文拟组合5,10,15,20-四(五氟苯基)氯化铁卟啉 (F₂₀TPPFeCl)和NHPI成接力氧化催化体系，以O₂为终端氧化剂，室温下实现环状苄胺的仿生氧化，从而发展构建异吲哚啉-1-酮和异喹啉-1-酮的绿色方法学。

本论文主要内容包括以下三个部分：

本论文的第一部分综述了异吲哚啉-1-酮和异喹啉-1-酮的合成进展，并对金属卟啉作为仿酶催化剂在氧化反应中的应用进行了总结，提出了本课题开展的思路。

本论文的第二部分开展了以F₂₀TPPFeCl/NHPI/O₂为催化体系对N-取代-3,4-二氢异喹啉类化合物进行氧化研究。发现该反应选择性高度依赖于N-取代类型，烷基和芳基不发生反应，只有拉电子的酰基才是适合的底物。通过对反应条件的优化和N-取代基的选择，优化条件如下：N-取代-3,4-二氢异喹啉：0.5 mmol、F₂₀TPPFeCl: 1 mol%、NHPI：0.1equiv.、乙酸乙酯（EA）：10 mL、室温、反应8小时，N-乙酰基-3,4-二氢异喹啉-1-酮的产率达到96%。在最优条件下，对1,2,3,4-四氢异喹啉进行底物拓展，合成了相应的N-取代-3,4-二氢异喹啉-1-酮衍生物，产率51%~96%。并开展了N-乙酰基-3,4-二氢异喹啉-1-酮衍生物水解研究，丰富了后官能团化的途径。最后通过机理实验，提出了环状苄胺的可能接力氧化机理。

本论文的第三部分主要开展了F₂₀TPPFeCl/NHPI/O₂体系对N-取代-异吲哚啉的催化氧化研究。进一步拓展了该催化氧化体系的底物适用范围。首先我们通过对异吲哚啉的酰化以及邻二甲苯衍生物的卤化、胺环合反应合成一系列N-取代-异吲哚啉底物，并在最优条件下对其进行了氧化研究，合成了一系列的异吲哚啉-1-酮衍生物，产率27%~82%。

实验结果表明，该催化体系对N-取代苄胺类底物具有良好的适用性，催化剂及催化体系环境友好，用量少，具有广阔的应用前景。

Isoindolin-1-one and isoquinolin-1-one are widely used as core backbones in natural products and important drug molecular structures. From the perspective of green chemistry and molecular diversity, it is particularly useful to develop general methods for constructing such structures. It is well known that synthetic metalloporphyrins are widely used as enzyme-like catalysts in the hydroxylation of benzyl C-H bonds. Similarly, N-hydroxyphthalimide (NHPI) can effectively mediate the activation of oxygen and be also widely used.  Based on the previous work in the laboratory, this paper intends to combine 5,10,15,20-tetrakis(pentafluorophenyl) ferric chloride porphyrin (F₂₀TPPFeCl) and NHPI to form a relay oxidation catalyst system, O₂ is used as the terminal oxidant, the method that the bionic oxidation of cyclic benzylamine is realized at room temperature, it is very important to develop a green methodology for the construction of isoindolin-1-one and isoquinolin-1-one.

The main content of this paper includes the following three parts:

In the first part of this paper, it is reviewed that the synthesis progress of isoindolin-1-one and isoquinolin-1-one and the application of metalloporphyrins as imitation enzyme catalysts in oxidation reactions. Based on these designs, this subject of the paper was proposed and we would carry out these ideas.

In the second part of this paper, we explored the method about the oxidation of N-substituted-3,4-dihydroisoquinoline compounds using F₂₀TPPFeCl/NHPI/O₂ as the catalytic system. We found that the reaction is highly dependent on the N-substitution type. The alkyl group and the aryl group do not react, and only the acyl group which is pull electrons is the suitable substrates. Through optimization of the reaction conditions and selection of N-substituents, it was finally determined the acetyl and propionyl as the most suitable substituents, and N-substituted-3,4-dihydroisoquinoline: 0.5 mmol, F₂₀TPPFeCl : 1 mol%, NHPI: 0.05 equiv., ethyl acetate (EA): 10 mL, room temperature, reaction for 8 hours, the yield of N-acetyl-3,4-dihydroisoquinolin-1-one reached 96%. Under the optimal conditions, we synthesized that the substrate extension of 1,2,3,4-tetrahydroisoquinoline and the corresponding N-substituted-3,4-dihydroisoquinolin-1-one derivatives, we had gotten the yield nearly 51% ~ 96%. The research on the hydrolysis of N-acetyl-3,4-dihydroisoquinolin-1-one derivatives was carried out, which enriched the pathway of post-functionalization.

In the third part of this paper, we continue to explore the method about the catalytic oxidation of N-substituted-isoindolin by F₂₀TPPFeCl/NHPI/O₂ system. The scope of the substrate for the catalytic oxidation system was further expanded. Firstly, we synthesized a series of N-substituted-isoindolin substrates through the acylation of isoindolin, the halogenation of o-xylene derivatives, and the amine cyclization reaction, and carried out oxidation studies on the optimal conditions. A series of isoindolin-1-one derivatives were synthesized with a yield of 27% ~ 82%.

Based on the above reaction results, we proposed that a possible relay oxidation mechanism of cyclic benzylamine.

The experimental results show that the catalytic system has good applicability to N-substituted benzylamine substrates, the catalyst and the catalytic system are environmentally friendly, the amount is small, and it has broad application prospects.

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