Palladium Catalyzed Cascade C-H Functionalization and NBS Mediated Thiocyanation Strategies for the Synthesis of Biologically Relevant Heterocycles and PACs
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2018
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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.
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.
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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, Palladium catalyzed, C-H functionalization, 5-Hydroxybenzofuran derivatives, Benzoquinone, Terminal alkyne, Intramolecular annulation, C-H bond alkenylation, copper acetate, Isoxazoline N-oxide, Thiocyanation, N-thiocyanosuccinamide, Isothiazole Derivatives