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研究生： 巴達禮
Pateliya Mujjamil Habib
論文名稱： GREENER APPROACHES TOWARDS THE SYNTHESIS OF PHARMACEUTICALLY ACTIVE N, O, S-HETEROCYCLES AND ANTIBACTERIAL AGENTS
GREENER APPROACHES TOWARDS THE SYNTHESIS OF PHARMACEUTICALLY ACTIVE N, O, S-HETEROCYCLES AND ANTIBACTERIAL AGENTS
指導教授： 姚清發
學位類別： 博士
Doctor
系所名稱： 化學系
Department of Chemistry
論文出版年： 2010
畢業學年度： 99
語文別： 英文
論文頁數： ?
中文關鍵詞： 在水中合成 、無催化劑 、抗菌劑
論文種類： 學術論文
相關次數： 點閱：132  下載：4 
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    • 本論文主要的目標是發展新的綠色化學的合成方式及抗菌劑的和成。
    　　此論文分成三個章節。第一章節分為兩部分，A部分是介紹不需使用催化劑，即可使吲哚加成至β-硝基苯乙烯。B部分則是介紹不需使用溶劑，即可使吡咯與吲哚加成至β-硝基苯乙烯。
    　　第二章節為利用在水中且無催化劑之條件下，促進吲哚與2-aryl-3-2H-chromenes進行烷基化反應。
    　　第三章節亦分為兩部分，A部分介紹有關[3+2]-環加成反應。B部分是介紹3-phenyl-5-((4-phenyl-2-(phenylimino)thiazol-3(2H)-yl)methyl)oxazo- lidin-2-one的合成。

    The dissertation is divided into three chapters. The first chapter is divided into two sections, Section A deals with the catalyst-free aqueous mediated conjugative addition of indoles to β-nitrostyrenes and Section B describes the conjugative addition of pyrrole and indole to β-nitroalkenes under solvent free condition (SFC). Second chapter provides a detailed study of “On-Water” promoted C-alkylation of indoles with 2-aryl-3-2H-chromenes under catalyst-free conditions’’ and mechanistic insights. Third chapter is divided into three sections A, B and C; Section A and B which describe the [3+2]-cycloaddition synthesis of 4-aryl-1,4-dihydrochromeno[4,3-d] [1,2,3]triazole and triazole-oxazolidinones derivatives respectively. Section C deals with the synthesis of a new class oxazolidinone C-5-(aryl-imino)thiazo and pharmacologically active Linezolid analogues.

    Abbreviations i-iii Abstract iv-ix Chapter one: Greener approach towards the synthesis of 3-(2-nitro-1- phenyl-ethyl)-1H-indole derivatives Section A : Catalyst free aqueous-mediated conjugative addition of indole to β-nitrostyrene. 1.1.1 Introduction 3 1.1.1.1 Innovation towards the greener solvents 3 1.1.1.2 Water as a solvent 4 1.1.2 Pharmacologically active Indole derivative 4 1.1.3 Synthetic utility of indolynitroalkane 6 1.1.4 Review of literature 6 1.1.5 Present work 13 1.1.5.1. Objective 13 1.1.5.2. Result and discussion 14 1.1.6 Plausible mechanism 18 1.1.7 Conclusion 18 1.1.8 Experimental procedure 19 1.1.9 References and notes 19 Section B : Conjugative addition of pyrrole and indole to β-nitroalkenes under solvent free condition (SFC) 1.2.1 Introduction 24 1.2.1.1 Solvent free condition (SFC) 24 1.2.1.2 Bioactive pyrrole derivatives 24 1.2.2 Review of literature 26 1.2.3 Present work 30 1.2.3.1 Objective 31 1.2.3.2 Results and discussion 31 1.2.4 Plausible mechanism 36 1.2.5 Conclusion 37 1.2.6 Experimental procedure 37 1.2.7 Spectral data 38 1.2.8 References and notes 47 Chapter Two: “On-Water”-Promoted C-Alkylation of Indoles with 2-Aryl-3- 2H-chromenes under Catalyst-Free Conditions’’ 2.1. Introduction 53 2.1.1 “On water” fast organic reaction 53 2.1.2 Bioactive chromen derivatives 57 2.2 Review of literature 58 2.3 Present work 59 2.3.1 Objective 63 2.3.2 Results and discussion 63 2.4 Stereochemistry and relative configuration of major/Minor disteromers. 66 2.5 Mechanism 73 2.6 D2O Experiment 74 2.7 Conclusion 75 2.8 Experimental procedure 75 2.9 Spectral data 75 2.10 Reference and notes 89 2.11 NOSY 94 2.12 Crystal XRD and refinement data 100 Chapter Three : Synthesis of N, S-Cantaining Five Membered Hetrocycles Section A : Catalyst-free 1, 3-dipolar cycloaddition of 3-nitrochromen with sodium azide: A facile method for the synthesis of 4-aryl-1,4-dihydro chromeno [4,3-d] [1,2,3] triazole derivatives 3.1.1 Introduction 119 3.1.1.1 Chromenes cantaning 1,2,3-Triazole heterocycles 120 3.1.1.2 1, 3 Dipolar cycloaddition 120 3.1.2 Review of literature 122 3.1.3 Present work 128 3.1.3.1 Objective 128 3.1.3.2 Results and discussion 129 3.1.4 Conclusion 134 3.1.5 Experimental 134 3.1.6 Spectral data 134 3.1.7 References 140 3.1.8 Crystal XRD and refinement data 143 Section B: A facile synthesis of triazole-oxazolidinones derivatives via One-pot three component reaction 3.2.1 Introduction 150 3.2.2 Review of literature 151 3.2.3 Present work 154 3.2.3.1 Objective 154 3.2.3.2 Results and discussion 155 3.2.3.3 Synthesis of bis-triazole-oxazolidine derivative 162 3.2.3.4 Synthesis of bis-triazole-oxazolidine 162 3.2.4 Synthesis of Antibacterial drug PH-027 163 3.2.5 Plausible mechanism 164 3.2.6 Conclusion 166 3.2.7 Experimental procedure 167 3.2.8 Spectral data 169 3.2.9 References 183 3.2.10 Crystal XRD and refinement data 188 Section C: New class Synthesis of Oxazolidinone C-5-(aryl-imino)-thiazo and Pharmacologically active Linerzolid analogues 3.3.1 Introduction 198 3.3.2 Review of literature 200 3.3.3. Present work 203 3.3.3.1 Objective 203 3.3.3.2 Retro synthetic analysis 204 3.3.3.3 Result and discussion 204 3.3.3.4 Synthesize the linezolid analogs 210 3.3.4 Mechanism 213 3.3.5 Conclusion 213 3.3.6 Experiment 214 3.3.7 Spectral data 217 3.3.8 Reference 225 3.3.9 Crystal XRD and refinement data 227 1H, 13C Spectra 240 4.1 Chapter I Spectra 241 4.2 Chapter II Spectra 295 4.3 Chapter III Spectra 367 List of publication 508

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