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研究生: 薩欽
Sachin Ichake
論文名稱: Palladium Catalyzed Cascade C-H Functionalization and NBS Mediated Thiocyanation Strategies for the Synthesis of Biologically Relevant Heterocycles and PACs
Palladium Catalyzed Cascade C-H Functionalization and NBS Mediated Thiocyanation Strategies for the Synthesis of Biologically Relevant Heterocycles and PACs
指導教授: 姚清發
Yao, Ching-Fa
學位類別: 博士
Doctor
系所名稱: 化學系
Department of Chemistry
論文出版年: 2018
畢業學年度: 106
語文別: 英文
論文頁數: 227
中文關鍵詞: 鈀催化C-H官能基5-羥基苯並呋喃衍生物苯醌末端炔烴分子內環C-H鍵烯基化乙酸銅異噁唑啉N-氧化物硫氰酸化N-硫代氰基琥珀酰胺異噻唑衍生物
英文關鍵詞: Palladium catalyzed, C-H functionalization, 5-Hydroxybenzofuran derivatives, Terminal alkyne, Intramolecular annulation, C-H bond alkenylation, copper acetate, Isoxazoline N-oxide, Thiocyanation, N-thiocyanosuccinamide, Isothiazole Derivatives
DOI URL: http://doi.org/10.6345/DIS.NTNU.DC.075.2018.B05
論文種類: 學術論文
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  • 本篇論文敘述了兩個部分。Part Ι分成三個部分。A部分闡述了鈀催化級聯C-H官能基化學反應的概況。在這個部分簡介了鈀催化級聯反應包含C-H鍵官能化,末端炔烴的C-H鍵官能化反應和鈀催化的C-H鍵烯基化。B部分描述了利用鈀金屬催化串聯C-H鍵官能化/環化策略來合成5種羥基苯並呋喃衍生物。在這個部分通過鈀催化的C-C / C-O鍵反應成功合成出5個羥基苯並呋喃衍生物。此外我們也描述了苯醌作為反應物和氧化劑的雙重作用。在C部分,表示鈀催化的分子內環化/脫氰氫化C-H鍵烯基化來合成苯[b]三亞苯衍生物。在乙酸銅作為氧化劑下利用鈀進行催化反應,有效的將苯氧乙酰甲基縮合產物(2Z,2'Z)-3,3' - ([1,1'-聯苯] -2,2'-二基)二(2-苯基丙烯腈)轉化為苯並[b] 苯並菲-9-腈衍生物。
    第二部分分為兩個部分。A部分是描述異噁唑啉N-氧化物。此外,我們也研究了各種C-S鍵形成的反應,也描述了硫氰化反應和硫氰酸化試劑的合成應用。此外,也討論了異噻唑類化合物的合成和應用。B部分,描述了“N-溴代琥珀酰亞胺介導的環己烯稠合異噁唑啉N-氧化物的硫氰化反應這是一種有效的新穎異噻唑衍生物的方法”。 此方法涉及原位生成的用作硫氰酸化劑的N-硫代氰基琥珀酰胺。此外,這種含SCN的產物進一步用於合成新的環己酮環稠合的異噻唑衍生物。

    The content of this dissertation is divided into two parts. Part Ι is subdivided into three sections. Section A illustrates the overview on Palladium catalyzed cascade C-H functionalization reactions. This section also described a brief survey on Palladium catalyzed cascade reactions involving C-H bond functionalization, C-H bond functionalization reactions of terminal alkynes and Palladium catalyzed C-H bond alkenylation protocols. Section B describes “The study of palladium-catalyzed tandem C−H bond functionalization/cyclization strategy for the synthesis of 5-Hydroxybenzofuran Derivatives”. In this section, the synthesis of 5-Hydroxybenzofuran Derivatives was achieved via palladium-catalyzed C-C/C-O bond formation reactions. Additionally, we also described the dual role of benzoquinone as a reactant as well as the oxidant. Section C demonstrates the “Palladium-Catalyzed Intramolecular Annulation/ Decyanogenative C-H bond Alkenylation Strategy for the Synthesis of Benzo[b] triphenylene derivatives”. Here, easily accessible knoevenagel condensation product (2Z,2'Z)-3,3'-([1,1'-biphenyl]-2,2'-diyl) bis(2-phenylacrylonitrile) converted efficiently into benzo[b]triphenylene-9-carbonitrile derivatives under palladium catalysis in the presence of copper acetate as an oxidant.
    Part II is divided into two sections. Section A is about the Overview on Isoxazoline N-oxides. Further, we also studied various C-S bond formation reactions, also described thiocyanation reactions and thiocyanating reagents and their synthetic utility in this section. additionally, Isothiazoles: synthesis and applications were discussed. Section B demonstrates the “N-Bromosuccinimide-Mediated Thiocyanation of Cyclohexene-Fused Isoxazoline N-Oxides: An Efficient Approach Towards the Novel Isothiazole Derivatives”. Present strategy involves In-situ generated N-thiocyanosuccinamide utilized as a thiocyanation agent. Moreover, this SCN containing product was further utilized for the synthesis of novel cyclohexanone ring fused isothiazole derivatives.

    Abbreviations i Abstract v Part-I Section-A: Overview on Palladium catalyzed Cascade Reactions Involving C-H bond functionalization I.A.1. Introduction 1 I.A.2. Palladium-catalyzed cascade reactions involving C-H bond functionalization 3 I.A.3. C-H bond functionalization reactions of terminal alkynes 7 I.A.4. Palladium-catalyzed C-H bond alkenylation reactions 10 I.A.6. References 12 Section B: Palladium-Catalyzed Tandem C−H Functionalization/Cyclization Strategy for the Synthesis of 5 Hydroxybenzofuran Derivatives I.B.1. Introduction 16 I.B.2. Review of literature 17 I.B.3. Result and discussions 21 I.B.4. Conclusion 31 I.B.5. Experimental Section 31 I.B.6. References 41 Section C: Palladium-Catalyzed Intramolecular Annulation/Decyanogenative C-H bond Alkenylation Strategy for the Synthesis of Benzo[b]triphenylene derivatives I.C.1. Introduction 44 I.C.2. Review of literature 44 I.C.3. Result and discussions 48 I.C.4. Conclusion 53 I.C.5. Experimental Section 54 I.C.6. References 68 Part II Section A: Overview on Isoxazoline N-oxide and Thiocyanation Reactions II.A.1. Isoxazoline N-oxides 71 II.A.2. C-S bond formation reactions 74 II.A.3. Outline on Thiocyanation reactions and reagents 77 II.A.4. Isothiazoles: synthesis and applications 79 II.A.5. Recent protocols on Isoxazoline N-oxide from our group 83 II.A.6. References 85 Section B: N-Bromosuccinimide-Mediated Thiocyanation of Cyclohexene-Fused Isoxazoline N-Oxides: An Efficient Approach Towards the Novel Isothiazole Derivatives II.B.1. Introduction 90 II.B.2. Review of literature 91 II.B.3. Result and discussions 92 II.B.4. Conclusion 103 II.B.5. Experimental Section 104 II.B.6. References 117 X-ray Crystallographic Data 120 1H and 13C NMR Spectral Copies 132 List of Publications 227

    Part I Section A(I.A.5.)

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    Part I Section B(I.B.6.)

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    Part I Section C(I.C.6.)

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