無催化劑條件下以β,γ-不飽和酮與鄰苯二胺環化合成1,5-苯二氮䓬類

Catalyst-Free Synthesis of 1,5-Benzodiazepines by Cyclocondensation of β,γ-Unsaturated Ketones with o-Phenylenediamine

朱彥睿(Yen-Ruei Zhu)

指導教授 ： 李世元

淡江大學/理學院/化學學系碩士班/碩士(2014年)

https://doi.org/10.6846/TKU.2014.01205

摘要

苯二氮䓬類化合物是一含雜環結構的化學分子，近年來因具有高度的生物活性而漸漸受到重視；如抗憂慮,抗抑鬱,抗發炎,抗病毒,抗愛滋病和抗微生物等等。以往文獻中苯二氮䓬類化合物合成製備多需利用催化劑來催化反應。因此我們嘗試開發無催化劑反應條件來合成1,5-苯二氮䓬類。我們實驗室以醛類化合物在金屬鎂與丙烯基溴進行超音波促進巴比艾爾反應形式加成得到丙烯基醇，加入氧化劑PCC將丙烯醇氧化成丙烯酮，更進一步與鄰苯二胺進行環化反應得到1,5-苯二氮䓬類。

關鍵字

1,5-苯二氮䓬類 ； 鄰苯二胺 ； 無催化劑 ； β,γ-不飽和酮

並列摘要

The benzodiazepines have attracted much attentions as pharmacophoric scaffold of heterocycles with a wide range of biological applications. These compounds are served as potentially biological compound with antianxiety, anti-depress, anti-inflammatory, anti-viral, anti-HIVand anti-microbial activities.Many synthetic methods for benzodiazepines have been reported,and mostly with the introduction of catalyst.
We developed a novel catalyst-free method synthetic of 1,5-benzodiazepines which was obtained under sonochemical Barbier-type reaction conditions. A reation mixture of activated magnesium powder, allyl bromide and aldehyde was sonicated to genterate allyl alcohol, followed by treatment of PCC to oxidize the allyl alcohol to allyl ketone.The cyclocondensation reaction of allyl ketone with o-phenylenediamine can produce 1,5-Benzodiazepines.

並列關鍵字

1,5-Benzodiazepine ； o-Phenylenediamine ； Catalyst-free Synthesis ； β,γ-Unsaturated ketone

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