利用金屬和非金屬催化劑合成具有生物活性之分子

Abstract

本論文的內容被分為三個章節，第一章節可被細分為三個部分，A部分主要是對於吲哚(indole)環的反應進行概述、分類及合成方法和相關文獻的說明。B部分的標題為「Carbazolones和2,3-disubstituted Indoles的簡易方法」，內容是介紹一個利用Fe/AcOH催化分子內還原3-hydroxy-2-(2-nitrophenyl)enones的含氮雜環化反應。C部分介紹2,3-disubstituted Indole在PdCl2催化下進行2-N-unprotected-2-alkynylanilines和多樣缺電子烯類的級聯反應(cascade reaction)。

第二章節介紹利用過渡金屬催化2-arylbenzoxazole衍生物和1,2,3-triazoles的合成。第二章節可被細分為三個部分，A部分主要是對於2-arylbenzoxazole衍生物進行概述、分類及合成方法的說明。此部分也對1,2,3-triazoles衍生物進行概述、分類及以azide和alkenes合成的方法說明。B部分介紹透過銅催化C-N和C-O鍵形成級聯反應，使2-arylbenzoxazole衍生物在芳香基團的鄰位上有胺或醯胺官能基的有效合成方法。C部分介紹一個新穎方法為透過銅催化在有氧環境下進行azide-alkene的氧化環加成反應。

第三章節介紹利用非金屬、過渡金屬催化合成naphthalene及其多元性導向的應用。第三章節可被細分為三個部分。A部分是naphthalene衍生物的概論及其合成方法。B部分描述一個有效率利用碘分子和2-(2-phenylethynyl)-Morita-Baylis-Hillman催化naphthalenes和iodo-substituted isochromene衍生物的合成。而iodo-substituted-derivatives則可以用來進行一連串的耦合反應如用硼酸、活化烯類、炔類分別可進行Suzuki coupling、Heck coupling、Sonogashira reaction。C部分介紹一個以PdCl2催化2-alkenylbenzaldehydes和缺電子烯類在有氧環境下分子間氧化環加成來合成naphthalenes的的有效路徑。The content of this dissertation is divided into three parts. The part I is subdivided into three sections. Section A, illustrate the overview, classification and synthetic approaches on ‘indole nucleus’ reactions and related literature review. Section B demonstrate the ‘An Easy Access to Carbazolones and 2,3-Disubstituted Indoles’ by a Fe/AcOH-mediated intramolecular reductive N-heteroannulation of 3-hydroxy-2-(2-nitrophenyl)enones. Section C, describes the synthesis of ‘2,3-disubstituted indoles’ via cascade reaction of 2-N-unprotected-2-alkynylanilines and various electron-deficient alkenes in the presence of PdCl2. Part II deals with the synthesis of 2-aryl benzoxazole derivatives and 1,2,3-triazoles by using transition metal catalyzed reactions. Part II is subdivided into three sections. Section A, deals with overview, classification and synthetic approaches of 2-aryl benzoxazole derivatives. This section also describe the overview on 1,2,3- triazole derivatives, classification and synthetic approaches from azide and alkenes. Section B, represents an efficient synthesis of 2-aryl benzoxazole derivatives having an amine or amide functionality in the aryl group at the ortho position via Copper-catalyzed tandem C–N and C–O bond formation. Section C, deals with the novel synthesis of substituted 1,2,3-triazoles via Copper(I)-catalyzed aerobic oxidative azide–alkene cycloaddition. Part III deals with the synthesis of naphthalene by using non-metal, transition metal catalyzed reactions and their application towards diversity oriented synthesis. Part III is subdivided into three sections. Section A, deals with overview and synthetic approaches towards naphthalene derivatives. Section B, describes an efficient synthesis of naphthalenes and iodo-substituted isochromene derivatives via reaction of 2-(2-phenylethynyl)-Morita-Baylis-Hillman adducts using molecular iodine. The resulting iodo-substituted-derivatives utilized to couple with a array of boronic acid (Suzuki coupling), activated alkene (Heck coupling) and alkyne (Sonogashira reaction). Section C, demonstrates an efficient synthesis of naphthalenes via PdCl2-catalyzed aerobic oxidative intermolecular cycloaddition between 2-alkenyl benzaldehydes and electron-deficient terminal alkenes.