路易斯酸輔佐環型2,3-環氧基炔醯胺、六環炔‒炔醯胺及呋喃炔醯胺化合物的環化反應：雙環㗁唑啶、螺旋γ-內醯胺與吡咯衍生物的合成
| dc.contributor | 葉名倉 | zh_TW |
| dc.contributor | Yeh, Ming-Chang | en_US |
| dc.contributor.author | 吳榮軒 | zh_TW |
| dc.contributor.author | Wu, Rong-Xuan | en_US |
| dc.date.accessioned | 2019-09-04T09:12:16Z | |
| dc.date.available | 不公開 | |
| dc.date.available | 2019-09-04T09:12:16Z | |
| dc.date.issued | 2018 | |
| dc.description.abstract | 本文分為三個主題，依序探討路易斯酸輔佐環型2,3-環氧基-1-炔醯胺化合物、六環炔‒炔醯胺化合物與呋喃炔醯胺化合物，分別合成雙環㗁唑啶、螺旋 γ-內醯胺與吡咯衍生物。 （1） 利用環型2,3-環氧基-1-炔醯胺化合物作為起始物，在氯化鋅輔佐下，密封管中進行分子內環化反應，得到具三個立體中心、單一（Z）構型的雙環㗁唑啶骨架化合物。此反應優點為操作簡單、產率高且得到唯一的立體異構物。 （2） 利用六環炔‒炔醯胺化合物作為起始物，在乾燥空氣及氯化亞鐵輔佐下進行分子內環化反應，得到氯取代的螺旋 γ-內醯胺化合物。此反應經由開環‒E2 消去反應‒aza-Prins-cyclization 系列形成氯取代的螺旋 γ-內醯胺化合物，優點為起始物製備容易與條件溫和。 （3） 利用金(III)催化呋喃炔醯胺化合物進行分子內環化反應，得到順式-3-(3-側氧基-3-芳香基-1-丙烯基)-4-苯基吡咯衍生物。此反應優點為條件溫和及反應時間短。 | zh_TW |
| dc.description.abstract | Three topics are discussed in this thesis. The Lewis acid-promoted cyclization reactions of cyclic 2,3-epoxy-1-ynamides, six-membered ring 1-yne-ynamides and ynamide-tethered furans afforded bicyclic oxazolidines, spiro γ-lactams and pyrrole derivatives, respectively. (1) The ZnCl2-promoted intramolecular cyclization reactions of aryl-substituted cyclic 2,3-epoxy-1-ynamides in a sealed tube yielded bicyclic oxazolidines containing three contiguous stereocenters with Z configuration. This methodology benefits from simple procedures, excellent yields, and a single stereoisomer of desired products. (2) The FeCl2-promoted intramolecular cyclization of alkyl or aryl-substituted six-membered 1-yne-ynamides under dry air afforded chlorinated spiro γ-lactams. The reaction mechanism was suggested to proceed via a ring-opening‒E2-elimination‒aza-prins-cyclization sequence, generating chlorinated spiro γ-lactams. The advantages of this reaction are mild reaction conditions and easily available of starting materials. (3) Gold(III)-catalyzed intramolecular cyclization reaction of ynamide-tethered furans afforded 3-((Z)-(3-aryl-3-oxopropen-1-yl) -4-phenyl-pyrrole derivatives. The advantages of this reaction are mild reaction conditions and short reaction times. | en_US |
| dc.description.sponsorship | 化學系 | zh_TW |
| dc.identifier | G060542056S | |
| dc.identifier.uri | http://etds.lib.ntnu.edu.tw/cgi-bin/gs32/gsweb.cgi?o=dstdcdr&s=id=%22G060542056S%22.&%22.id.& | |
| dc.identifier.uri | http://rportal.lib.ntnu.edu.tw:80/handle/20.500.12235/100205 | |
| dc.language | 中文 | |
| dc.subject | 路易斯酸 | zh_TW |
| dc.subject | 氯化鋅 | zh_TW |
| dc.subject | 雙環㗁唑啶 | zh_TW |
| dc.subject | 炔‒炔醯胺 | zh_TW |
| dc.subject | 氯化亞鐵 | zh_TW |
| dc.subject | 螺旋γ-內醯胺 | zh_TW |
| dc.subject | 三氯化金 | zh_TW |
| dc.subject | 吡咯 | zh_TW |
| dc.subject | Lewis acid | en_US |
| dc.subject | zinc chloride | en_US |
| dc.subject | bicyclic oxazolidine | en_US |
| dc.subject | yne-ynaminde | en_US |
| dc.subject | iron(II) chloride | en_US |
| dc.subject | spiro γ-lactam | en_US |
| dc.subject | gold(III) chloride | en_US |
| dc.subject | pyrrole | en_US |
| dc.title | 路易斯酸輔佐環型2,3-環氧基炔醯胺、六環炔‒炔醯胺及呋喃炔醯胺化合物的環化反應：雙環㗁唑啶、螺旋γ-內醯胺與吡咯衍生物的合成 | zh_TW |
| dc.title | Lewis Acid-Promoted Cyclization Reactions of Cyclic 2,3-Epoxy-1-ynamides, Six-Membered Ring Yne-Ynamides, and Ynamide-Tethered Furans: Synthesis of Bicyclic Oxazolidines, Spiro γ-Lactams, and Pyrrole Derivatives. | en_US |