葉名倉Yeh, Ming-Chang吳榮軒Wu, Rong-Xuan2019-09-04不公開2019-09-042018http://etds.lib.ntnu.edu.tw/cgi-bin/gs32/gsweb.cgi?o=dstdcdr&s=id=%22G060542056S%22.&%22.id.&http://rportal.lib.ntnu.edu.tw:80/handle/20.500.12235/100205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。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.路易斯酸氯化鋅雙環㗁唑啶炔‒炔醯胺氯化亞鐵螺旋γ-內醯胺三氯化金吡咯Lewis acidzinc chloridebicyclic oxazolidineyne-ynamindeiron(II) chloridespiro γ-lactamgold(III) chloridepyrrole