利用高價碘(III)試劑進行雜環之合成研究

Hypervalent Iodine(III) Reagent Mediated Synthesis of Heterocycles

林玉千(Yu-Chien Lin)

指導教授 ： 陳麟慶

高雄醫學大學/藥學院/藥學研究所/碩士(2005年)

摘要

近年來，高價碘試劑受到廣泛的矚目是由於具有低毒性、處理簡便及使用方便的特點。而其中phenyliodine(III) bis (trifluoroacetate) (PIFA)、phenyliodine(III) diacetate (PIDA)、and [hydroxy(tosyloxy)iodo] -benzene (HTIB)等最常被使用在合成化學上。
Pictet-Spengler 縮合反應是合成1,2,3,4-tetrahydroisoquinoline有效的合成法之ㄧ，我們利用α-(methylthio)-N-methoxy- N-methylacetamide與PIFA 進行Pictet-Spengler 縮合反應的修飾合成N-methoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamides。
除此之外，內酯環化在有機合成上扮演一個極為重要角色，因為內酯環不僅具備許多重要的生理活性，在自然界含量豐富，而且還是合成上有用的組元(synthon)。在這部份的實驗中，我們將介紹一個直接、有效的方法，利用4-benzoyibutyric acids與phenyliodine(III) triflate在室溫攪拌下進行5-benzoyldihydro-2(3H)-furanones的製備。

關鍵字

高價碘(III)試劑 ； Pummerer 反應 ； Pictet-Spengler 反應

並列摘要

In recent years, hypervalent iodine reagents have attracted much attention as useful synthetic reagent. These hypervalent iodine reagents have been extensively used in organic synthesis due to their low toxicity, ready availability and easy handing. In the family of hypervalent iodine compounds, phenyliodine(III) bis (trifluoroacetate) (PIFA)、phenyliodine (III) diacetate (PIDA)、and [hydroxy(tosyloxy)iodo]benzene (HTIB) are the most frequently used and easily available reagents.
Pictet-Spengler reaction is one of the fundamental reaction for preparation of 1,2,3,4,-tetrahydroisoquinolines. We reported here a modified Pictet-Spengler cyclization of α-(methylthio)-N-methoxy- N-methylacetamide using PIFA to prepare N-methoxy-N-methyl- 1,2,3,4-tetrahydroisoquinoline-1-carboxamides.
On the other hand, lactonization methodology plays an important role in modern organic synthetic chemistry not only because lactones are important constituent in biologically active natural products, but also because they constitute a particularly useful class of synthons. In this work, a new and directly method for the conversion of 4-benzoyibutyric acids to 5-benzoyldihydro-2(3H)-furanones by the reaction with phenyliodine(III) triflate at room temperature.

並列關鍵字

Pummerer reaction ； Pictet-Spengler reaction ； phenyliodine(III) bis (trifluoroacetate)

參考文獻

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(c) Koser, G. F. in The Chemistry of Functional Groups, Supplement D, Patai, S.; Rappoport, Z.. Ed.; Wiley: New York, 1983, Ch. 18 and 25.