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.contributorYeh, Ming-Changen_US
dc.contributor.author吳榮軒zh_TW
dc.contributor.authorWu, Rong-Xuanen_US
dc.date.accessioned2019-09-04T09:12:16Z
dc.date.available不公開
dc.date.available2019-09-04T09:12:16Z
dc.date.issued2018
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.abstractThree 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.identifierG060542056S
dc.identifier.urihttp://etds.lib.ntnu.edu.tw/cgi-bin/gs32/gsweb.cgi?o=dstdcdr&s=id=%22G060542056S%22.&%22.id.&
dc.identifier.urihttp://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.subjectLewis aciden_US
dc.subjectzinc chlorideen_US
dc.subjectbicyclic oxazolidineen_US
dc.subjectyne-ynamindeen_US
dc.subjectiron(II) chlorideen_US
dc.subjectspiro γ-lactamen_US
dc.subjectgold(III) chlorideen_US
dc.subjectpyrroleen_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.titleLewis 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

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