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研究生: 雷姆希
Chintakunta Ramesh
論文名稱: 應用硝基苯類化合物為原料並經由分子內還原及環化反應來製備具有生物活性的含氮雜環化合物
Synthesis of Biologically Active N-Heterocycles via Intramolecular Reductive Cyclizations Of Nitroaromatics
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: 2011
畢業學年度: 100
語文別: 英文
論文頁數: 315
中文關鍵詞: 還原環化貝里斯-希爾曼反應氮雜環鐵/醋酸硝基苯
英文關鍵詞: Reductive Cyclization, Baylis-Hillman Reaction, N-Heterocyles, Fe/AcOH, Nitroaromatics
論文種類: 學術論文
相關次數: 點閱:323下載:4
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  • 在有機化學合成領域的研究中,開發具有高效率和新穎的合成方式來合成含氮的雜環化合物是相當重要的,因為其具有廣泛的生物活性和在醫藥以及藥物化學領域的潛在應用性。在這個方面,以鄰位硝基芳香族化合物準備作為可行的起始物,藉由環化和還原反應來合成建構出多樣性的含氮原子之雜環分子。
    本論文主要分為四個章節。在第一章節,回顧有關於使用在醋酸中加入鐵粉以進行分子內環化和還原反應的相關文獻報導。在第二章節,主要是分為兩個部分,其中A部分是以新的合成方式,使用經過Baylis-Hillman reaction所得到的產物與indoles衍生物來進行碳-碳鍵的烷化反應,以合成出具有indole取代基的quinolines衍生物;B部分則是使用經過Baylis-Hillman reaction所得到的產物與indoles衍生物來進行碳-碳鍵的烷化和環化反應,以合成出具有indole取代基的吖啶以及indolylcyclopenta[b]quinoline的衍生物。在第三章節,主要是分為兩個部分,其中A部分是使用嶄新的合成路徑,在鐵粉/醋酸的條件下,使用3-(2-nitro-1-(2-nitrophenyl)ethyl)-1H-indoles來進行環化以及還原反應,合成出3,3'-biindoles之衍生物;B部分是使用簡潔的合成路徑,在鐵粉/醋酸的條件底下,合成出quinolines的衍生物。第四章節,同樣分為兩個部分,A部分是使用簡單和便利的合成路徑,在鐵粉/醋酸的條件底下,藉由2-(2-nitrophenoxy)acetonitrile經由環化和還原反應,合成出2H-1,4-benzoxazin-3-(4H)-ones的衍生物;B部分主要是使用具有高效率的“點擊”反應,藉由一價銅催化反應,將含有2H-1,4-benzoxazin-3-(4H)-one基團,合成出在1號位和4號位具有雙取代的1,2,3-三氮唑類衍生物。

    The development of efficient and novel protocols for the construction of N-heterocycles is fascinating and important area of research in synthetic organic chemistry due to their wide spectrum of biological activities and potential application in pharmaceutical field as well as in medicinal chemistry. In this respects, the o-nitro aromatics are readily available starting materials for the construction various nitrogen containing heterocyclic molecules via reductive cyclization.

    The contents of this dissertation is divided into four chapters, the Chapter I deals with overview on reductive cyclization and literature survey on intramolecular reductive cyclization in the presence of Fe powder in acetic acid. The Chapter II subdivided into two sections, section A deals with novel synthesis of indolylquinoline derivatives via the C-alkylation of Baylis-Hillman adducts and section B deals with novel synthesis of indolylacridines and indolylcyclopenta[b]quinoline derivatives from the C-alkylated cyclic Baylis-Hillman adducts. The Chapter III subdivided into two sections, section A deals with an unprecedented route for the synthesis of 3,3'-biindoles via reductive cyclization of 3-(2-nitro-1-(2-nitrophenyl)ethyl)-1H-indoles mediated by Fe/AcOH and Section B deals with Fe/AcOH mediated carbon degradation: a facile route for the synthesis of quinoline derivatives. The Chapter IV subdivided into two sections, section A deals with a simple and facile route for the synthesis of 2H-1,4-benzoxazin-3-(4H)-ones via reductive cyclization of 2-(2-nitrophenoxy)acetonitrile adducts in the presence of Fe/AcOH and section B deals with a highly efficient “ Click ” approach to synthesis of 1,4-disubstituted 1,2,3-triazole analogues containing 2H-1,4-benzoxazin-3-(4H)-one moiety via a copper (I)-catalyzed reaction.

    Abbreviations i-iv Abstract v-xiii Chapter-I : Overview on Reductive Cyclization I.1. Introduction 1 I.2. Fe/AcOH as Reductive Cyclizing agent 3 I.2.1. Reduction of aromatic nitro groups 4 I.2.2. Reduction of aliphatic nitro groups 13 I.3.References 15 Chapter-II, Section A: Novel synthesis of indolylquinoline derivatives via the C-alkylation of Baylis-Hillman adducts II.A.1. Introduction 20 II.A.2. Review of Literature 21 II.A.3. Results and Discussions 26 II.A.4. Conclusion 32 II.A.5. Experimental Section 33 II.A.6. References 43 Chapter-II, Section B: Application of the Baylis-Hillman Reaction: An Unprecedented in situ [1,3] sigmatropic rearrangement of indole nucleus to access novel indolylacridine and indolyl cyclopenta[b]quinoline derivatives II.B.1. Introduction 47 II.B.2. Review of Literature 48 II.B.3. Results and Discussions 50 II.B.4. Conclusion 60 II.B.5. Experimental Section 60 II.B.6. References 70 Chapter-III, Section A: An unprecedented route for the synthesis of 3,3'-biindoles via reductive cyclization of 3-(2-nitro-1-(2-nitrophenyl)ethyl)-1H-indoles mediated by Fe/AcOH III.A.1. Introduction 74 III.A.2. Review of Literature 75 III.A.3. Results and Discussions 78 III.A.4. Conclusion 83 III.A.5. Experimental Section 84 III.A.6. References 89 Chapter-III, Section B: Fe/AcOH mediated carbon degradation: a facile route for the synthesis of quinoline derivatives III.B.1. Introduction 92 III.B.2. Review of Literature 93 III.B.3. Results and Discussions 96 III.B.4. Conclusion 102 III.B.5. Experimental Section 102 III.B.6. References 108 Chapter-IV, Section A: A simple and facile route for the synthesis of 2H-1,4-benzoxazin-3-(4H)-ones via reductive cyclization of 2-(2-nitrophenoxy) aceto nitrile adducts in the presence of Fe/AcOH IV.A.1. Introduction 111 IV.A.2. Review of Literature 112 IV.A.3. Results and Discussions 114 IV.A.4. Conclusion 119 IV.A.5. Experimental Section 119 IV.A.6. References 128 Chapter-IV, Section B: A Highly Efficient “ Click ” Approach to Synthesis of 1,4-Disubstituted 1,2,3-Triazole analogues containing 2H-1, 4-benzoxazin-3-(4H)-one Moiety Via a Copper (I)-Catalyzed Reaction IV.B.1. Introduction 131 IV.B.2. Review of Literature 132 IV.B.3. Results and Discussions 133 IV.B.4. Conclusion 145 IV.B.5. Experimental Section 145 IV.B.6. References 158 X-Ray Crystallographic Data and NMR Spectra 162 List of Publications 315

    Chapter-I
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