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Short and tandem syntheses of spiro[2.5]octane-5,7-dione and spiro[3.5]nonane-6,8-dione via diethyl acetonedicarboxylate
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2015-09-30 , DOI: 10.1016/j.tetlet.2015.09.132
Xiangle Jin , Wei Xu , Jinsong Yang , Jun Lu , Yan Fu , Le Xie , Qian Zhu , Weitong Dong

A general synthetic route to spiro[2.5]octane-5,7-dione and spiro[3.5]nonane-6,8-dione that involves cyclization of the related acrylates and diethyl acetonedicarboxylate, followed by decarboxylation, has been developed. Compared with previous synthetic methods, the developed protocol avoids the use of column chromatography in each of the synthetic steps. Therefore, it can be readily scaled-up. The use of diethyl acetonedicarboxylate under mild conditions to build the skeleton of 1,3-cyclohexanedione has proved to be very efficient.



中文翻译:

通过丙酮二羧酸二乙酯短和串联合成螺[2.5]辛烷-5,7-二酮和螺[3.5]壬烷-6,8-二酮

已经开发了合成螺[2.5]辛烷-5,7-二酮和螺[3.5]壬烷-6,8-二酮的一般合成途径,该方法涉及将相关的丙烯酸酯和丙酮二羧酸二乙酯环化,然后脱羧。与以前的合成方法相比,开发的方案避免了在每个合成步骤中使用柱色谱法。因此,它可以很容易地按比例放大。事实证明,在温和的条件下使用丙酮二甲酸二乙酯构建1,3-环己二酮的骨架非常有效。

更新日期:2015-09-30
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