一鍋化合成硝基環丙烷之研究

Abstract

硝基環丙烷不只是可以合成複雜有機分子的前驅物，也是許多具有生物活性的天然物或非天然物的基礎結構。我們的合成策略是使用丙二酸二乙酯(Diethyl malonate)和硝基苯乙烯(β-Nitrostyrene)作為起始物，先加入鹼進行Michael加成反應後，再加入N-溴代丁二醯亞胺(N-Bromosuccinimide, NBS)作為溴化試劑生成含有溴的中間體，最後利用鹼進行分子內環化反應便可得到硝基環丙烷產物。而我們可以藉由使用不同的硝基烯烴作為起始物以合成產率不錯的一系列硝基環丙烷產物。

Nitrocyclopropane is not only a precursor for the synthesis of complex organic molecules, but also the basic structure of many biologically active natural or non-natural substances. This developed synthetic process involves the Michael addition of diethyl malonate to various nitroolefins, followed by bromination with N-bromosuccinimide to generate a bromine-containing intermediate. Then, the brominated adduct is added with a base for intramolecular cyclization to obtain the highly functionalized nitrocyclopropanes product in moderate to good yields. We have pioneered a high-efficiency method for synthesizing nitrocyclopropane, which is easy to operate, and the reagents used in the process are all commercially available and cheap reagents.