Preparation of trifluoromethylated dihydrocoumarins, indanones, and arylpropanoic acids by tandem superacidic activation of 2-(trifluoromethyl)acrylic acid with arenes.
Preparation of trifluoromethylated dihydrocoumarins, indanones, and arylpropanoic acids by tandem superacidic activation of 2-(trifluoromethyl)acrylic acid with arenes.
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DOI：
10.1021/jo9026275
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发表时间：
2010-03
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通讯作者：
G. Prakash;F. Paknia;Habiba Vaghoo;G. Rasul;T. Mathew;G. Olah
中科院分区：
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作者：
G. Prakash;F. Paknia;Habiba Vaghoo;G. Rasul;T. Mathew;G. Olah
茚酮和香豆素是合成许多药物和生物活性化合物的重要中间体。含氟有机物在设计非常有效的治疗剂中起着至关重要的作用，这是由于这些分子中氟的存在显著增强了其亲脂性、生物利用度和快速吸收。在此，我们报告了一种高效的一锅法合成三氟甲基化芳基丙酸、二氢茚酮和二氢香豆素的方法，该方法使用芳烃/苯酚与2-（三氟甲基）丙烯酸在超酸性条件下使用三氟甲磺酸进行傅-克烷基化或串联傅-克烷基化-环酰化反应。用从头算方法计算了反应中间体的结构能，结果得到了合理的解释。
Indanones and coumarins are important intermediates for the convenient synthesis of many pharmaceutical and biologically active compounds. Fluoroorganics play a vital role in the design of very effective therapeutics due to significant enhancenment in their lipophilicity, bioavailability, and fast uptake by the presence of fluorine in these molecules. Herein, we report an efficient one-pot synthesis of trifluoromethylated arylpropanoic acids, indanones, and dihydrocoumarins using Friedel-Crafts alkylation or tandem Friedel-Crafts alkylation-cycloacylation of arenes/phenols with 2-(trifluoromethyl)acrylic acid under superacidic conditions using trifluoromethanesulfonic acid. The results have been rationalized by the structure energy calculations of the involved reaction intermediates using ab initio theoretical methods.