Microwave-assisted fluorination of 2-acylpyrroles: synthesis of fluorohymenidin.
Microwave-assisted fluorination of 2-acylpyrroles: synthesis of fluorohymenidin.
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DOI：
10.1021/ol2029993
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发表时间：
2012-01
期刊：
影响因子：
5.2
通讯作者：
Benjamin Troegel;T. Lindel
中科院分区：
文献类型：
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作者：
Benjamin Troegel;T. Lindel
用选择性氟在微波条件下处理单和非溴化2-酰基吡咯，导致吡咯环的5位氟化。特别是，2-三氯乙酰化吡咯可以氟化。以合成二氢氟膜酸酐为例，经脱氢制得氟膜酸酐，成为第一个氟化吡咯-咪唑生物碱。乙烯基双键的引入是通过氯化2-氨基咪唑部分，然后在100℃的DMF中脱氢氯化实现的。
Treatment of mono- and nonbrominated 2-acylpyrroles with Selectfluor under microwave conditions leads to fluorination of the pyrrole ring in the 5-position. In particular, 2-trichloroacetylated pyrrole can be fluorinated. As an example, dihydrofluorohymenidin was synthesized and dehydrogenated to fluorohymenidin as the first fluorinated pyrrole-imidazole alkaloid. Introduction of the vinyl double bond was achieved by chlorination of the 2-aminoimidazole moiety, followed by dehydrochlorination at 100 °C in DMF.