3-亚烷基(亚芳基)异苯并呋喃-1(3H)-酮及其衍生物的合成研究
收稿日期: 2013-12-09
修回日期: 2014-03-12
网络出版日期: 2014-05-26
Synthesis of 3-Alkylidene(arylidene)isobenfuran-1(3H)-one and Their Derivatives
Received date: 2013-12-09
Revised date: 2014-03-12
Online published: 2014-05-26
报道了3-亚烷基(亚芳基)异苯并呋喃-1(3H)-酮及其衍生物的简易而且高效的合成方法. 其特点是原料易得、价格低廉、反应条件温和、收率高. 该方法以异苯并呋喃-1(3H)-酮(苯酞)及其衍生物为原料，经过自由基溴代合成了3-溴异苯并呋喃-1(3H)-酮及其衍生物，随后与三苯基膦发生亲核取代反应，接着在三乙胺的作用下发生消除反应生成Wittig试剂，最后与脂肪族醛或者芳香族醛发生Wittig反应得到目标化合物. 目标产物及其中间体有13个是新化合物.
关键词： 3-亚烷基(亚芳基)异苯并呋喃-1(3H)-酮; 衍生物; 季鏻盐; Wittig反应; 合成
郑纯智 , 朱星星 , 赵德建 , 贾洪斌 , 张继振 . 3-亚烷基(亚芳基)异苯并呋喃-1(3H)-酮及其衍生物的合成研究[J]. 有机化学, 2014 , 34(9) : 1881 -1888 . DOI: 10.6023/cjoc201312011
This paper reports a novel and highly efficient synthesis of 3-alkylidene(arylidene)isobenzofuran-1(3H)-one and the corresponding derivatives. The new method is characterized with raw material easy to get, low manufacturing cost, mild reaction conditions and high yields. Isobenzofuran-1(3H)-one (phthalide) and their derivatives were used as starting material. After reacted through free-radical bromination with N-bromobutanimide (NBS), the starting materials were converted to the corresponding 3-bromoisobenzofuran-1(3H)-one and their derivatives, followed by nucleophilic substitution with triphenylphosphine. Then the corresponding Wittig reagents were obtained through elimination reaction by triethylamine, which further react with fatty aldehydes or aromatic aldehydes to afford the target compounds. Thirteen target products and intermediates are new compounds.
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