葉名倉Yeh, Ming-Chang游昀潔Yu, Yun-Chieh2020-10-192021-01-012020-10-192020http://etds.lib.ntnu.edu.tw/cgi-bin/gs32/gsweb.cgi?o=dstdcdr&s=id=%22G060742014S%22.&%22.id.&http://rportal.lib.ntnu.edu.tw:80/handle/20.500.12235/111130本文分為二個主題，依序討論以三氯化銦輔佐共軛烯炔－炔醯胺化合物進行分子內環化反應及二溴化鐵輔佐4-炔醯胺環己-2-烯-1-酮進行分子內麥可加成反應（Michael-Addition），分別得到δ-內醯胺與稠環γ-內醯胺衍生物。 （一） 利用三氯化銦進行輔佐，可以使共軛烯炔－炔醯胺化合物進行分子內環化反應，合成出δ-內醯胺衍生物。此反應的優點是：起始物製備容易、反應條件溫和、不須添加氧化劑及反應時間短。 （二） 利用二溴化鐵輔佐4-炔醯胺環己-2-烯-1-酮，於氮氣回流的條件下進行環化反應，反應先形成keteniminium中間體I，溴陰離子再親核性加成至keteniminium中間體α位置的碳上，接著再進行分子內麥可加成反應，在反應終止後，即可得到稠環γ-內醯胺衍生物。此反應的優點是：具有良好的立體選擇性及在進行環化反應時不須額外添加氧化劑。 關鍵字：炔－炔醯胺、三氯化銦、銦(III)、δ-內醯胺、2-環己烯-1-酮、二溴化鐵、稠環γ-內醯胺This thesis conatins two topics. Indium(III) chloride-assisted cyclization of ynamido-tethered conjugated ene-ynes generated δ-lactam derivatives and iron(II) bromide-mediated Michael-addition of 4-yne-amido-cyclohex-2-en-1-ones yielded bicyclic γ-lactam derivatives. (1) Indium(III) chloride assisted cyclization of ynamido-tethered conjugated ene-ynes furnishes δ-lactams. The reactions feature procedurally simple, producing the products under the mild conditions without additional oxidants and with short reaction time. (2) Treatment of iron(II) bromide with 4-yne-amido-cyclohex-2-en-1-ones under nitrogen at reflux affords bicyclic γ-lactams. Activation of ynamide with FeBr2 gives the keteniminium ion I, which was trapped by a bromide ion at the α-potision to afford intermediate II. Intramolecular Michael-Addition of II gives the bicyclic γ-lactams. The reactions feature excellent diastereoselectivity and producing the products without additional oxidants. Keywords：yne-ynamides、indium(III) chloride、indium(III)、δ-lactams、cyclohex-2-en-1-ones、iron(II) bromide、bicyclic γ-lactams炔－炔醯胺三氯化銦銦(III)δ-內醯胺2-環己烯-1-酮二溴化鐵稠環γ-內醯胺yne-ynamidesindium(III) chlorideindium(III)δ-lactamscyclohex-2-en-1-onesiron(II) bromidebicyclic γ-lactams