將2,3,7-三氮-二環[3.3.0]辛-2-烯類衍生物進行逆環化加成反應製備1,3-取代基吡咯的研究

Study on the Preparation of 1,3-disubstituted pyrrole from 2,3,7-triazabicyclo[3.3.0]oct-2-ene Derivatives by Retro Dipolar Cycloaddition

范耿維(Keng-Wei Fan)

指導教授 ： 楊嘉喜

中原大學/理學院/化學系/碩士(2009年)

https://doi.org/10.6840/cycu200900009

摘要

吡咯在不同碳上接上不同取代基這類型結構的化合物通常具有生物活性，在藥物上通常具有藥物活性，是個重要的中間體，例如消炎鎮痛、降低血糖、抑制胃酸等等功用。
本文是將2,3,7-三氮-二環[3,3,0]辛-2-烯類衍生物與氯化亞銅為催化劑（Catalyst）、疊氮化鈉為配位基（Ligands）下進行Retro Dipolar Cycloaddition得到1,3-取代基吡咯。並且在本實驗中討論其反應條件，改變其溫度、反應時間、催化劑、溶劑等條件，嘗試改善提高產率。
大部分合成吡咯的文獻中都是以合成方式製備，幾乎沒有以逆環化反應的方式來製備合成吡咯。Retro Dipolar Cycloaddition進行開環的反應在文獻上是不多的，尤其以亞銅為催化劑（Catalyst）進行開環反應的文獻，更是少之又少。

關鍵字

?咯 ； 逆環化加成反應

並列摘要

Derivatives of pyrrole often have biological activities, and are important in pharmacology. For example pyrrole moiety appears in pharmaceuticals as anti-inflammatory and analgesic agent, drug having blood sugar decreasing, gastric juics apoleti activity.

In this study, 2,3,7-triaza-bicyclo[3.3.0] oct-2-ene derivaties, in the presence of cuprous chloride as the catalyst, and the sodium azide as ligands, undergo Retro Dipolar Cycloaddition reaction, to give 1,3-disubstituted pyrroles. The reaction conditions, such as temperature, reaction time, catalyst and solvent, on the reaction are discussed.

In the synthesis of pyrrole, literature is by synthesizes the way preparation, does not have the way which takes off to prepare the synthesis pyrrole nearly. It is hard to find the research about Retro Dipolar Cycloaddition. Especially in this study in using cuprous chloride as catalyst to open ring reaction is not often see.

並列關鍵字

pyrrole ； Retro Dipolar Cycloaddition

參考文獻

1. Kleemann, H.W. US Patent. 2003, 7078414

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14. 中原大學化學研究所廖經互之碩士論文,（民國九十四年六月）