New Method for the Synthesis of Diversely Functionalized Imidazoles from N-Acylated α-Aminonitriles
New Method for the Synthesis of Diversely Functionalized Imidazoles from N-Acylated α-Aminonitriles
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DOI：
10.1021/ol036423y
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发表时间：
2004-02
期刊：
影响因子：
5.2
通讯作者：
Y. Zhong;Jaemoon Lee;R. Reamer;D. Askin
中科院分区：
文献类型：
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作者：
Y. Zhong;Jaemoon Lee;R. Reamer;D. Askin
本文报道了一种由N-酰化α-氨基腈合成具有重要药用价值的双硫代咪唑类化合物的新方法。N-酰化的α-氨基腈与三苯基膦和四卤化碳反应，得到2，4-二取代的5-卤代-1H-咪唑。将该方法应用于2-丁基-4-氯-5-羟甲基咪唑的合成。这些卤代咪唑可以通过钯催化的偶联反应直接转化为2，4，5-三取代咪唑。
A new general method for the synthesis of medicinally important diversely functionalized imidazoles from N-acylated α-aminonitriles has been developed. N-Acylated α-aminonitriles were reacted with triphenylphosphine and carbon tetrahalide to afford 2,4-disubstituted 5-halo-1H-imidazoles in good yield. This new methodology was applied for the synthesis of 2-butyl-4-chloro-5-hydroxymethylimidazole. These halo-imidazoles can be directly converted to 2,4,5-trisubstituted imidazoles through palladium-catalyzed coupling reactions.