Nikolay A. Zinovyev, Irina P. Beletskaya, Igor D. Titanyuk
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引用次数: 0
摘要
通过改良重氮转移反应，可以轻松制备出多种 α-芳基-α-重氮膦酸盐。在叔丁醇钾（KOtBu）存在下，苄基膦酸盐与甲苯磺酰叠氮（TsN3）反应生成重氮膦酸盐，收率高达 93%（一般为 70-80%）。通过与烷基丙烯酸酯进行 1,3-二极环加成，然后进行 NaH 处理，成功探索了芳基二氮膦酸盐在一锅内合成 5-芳基取代的吡唑-3-羧酸盐的方法。第二阶段是消除二乙氧基磷酸基并进行芳香化循环。
1,3-Dipolar Cycloaddition of Diazophosphonates with Methyl(Ethyl) Acrylate for the Synthesis of 5-Arylpyrazole-3-carboxylates
A wide range of α-aryl-α-diazophosphonates were easily prepared via modified diazo transfer reaction. Benzylphoshonates reacted with tosyl azide (TsN3) in the presence of potassium tert-butoxide (KOtBu) to afford diazophosphonates in yields up to 93% (generally 70–80%). Aryldiazophosponates were successfully explored for the synthesis of 5-aryl-substituted pyrazol-3-carboxylates in one pot by the 1,3-dipolar cycloaddition with alkyl acrylates followed by NaH treatment. The second stage led to elimination of the diethoxylphosphoryl moiety with the aromatization of cycle.
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