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中南大学学报(自然科学版)

Journal of Central South University

第49卷    第5期    总第285期    2018年5月

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文章编号:1672-7207(2018)05-1062-10
邻亚甲基醌和3-氯吲哚啉酮[4+1]环加成合成螺环吲哚啉酮
杜升华1, 2,周吉2,江国防2

(1. 湖南化工研究院有限公司,湖南 长沙,410014; 2. 湖南大学 化学化工学院,湖南 长沙,410082)

摘 要: 以3-氯吲哚啉酮与邻亚甲基醌中间体为原料,在碱性条件下通过Michael加成/环化串联反应,高收率、高非对映选择性地构建双杂环螺环化合物。其中,邻亚甲基醌中间体通过磺酰基取代苯酚在无机碱作用下原位生成获得,在温和、简易操作条件下与3-氯吲哚啉酮作用一步制备含有苯并呋喃和吲哚啉酮这2种重要杂环骨架结构的螺环化合物。通过条件筛选,在最优条件下获得目标产物。为了验证此方法的实用性,进行克级规模试验。研究结果表明:在最优条件下,目标产物收率高达92%,非对映选择性dr大于20:1;扩大底物用量,收率和非对映选择性仍很高;此方法普适性广,对于多种类型的磺酰基取代苯酚以及吲哚啉酮底物同样适用。

 

关键字: 3-氯吲哚啉酮;邻亚甲基醌中间体;Michael加成/环化串联反应;螺环吲哚啉酮化合物

Synthesis of spirooxindoles through [4+1] cycloaddition of ortho-quinone methides with 3-chlorooxindoles
DU Shenghua1, 2, ZHOU Ji2, JIANG Guofang2

1. Hunan Research Institute of Chemical Industry Co. Ltd., Changsha 410014, China; 2. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China

Abstract:The spirooxindoles were synthesized in high yield with excellent diastereoslectivities using 3-chlorooxindoles and ortho-quinone methides (o-QMs) as materials through the Michael addition/cyclization cascade process under basic condition. To get the two spirocyclic compound involving benzofuran and oxindole skeletons under mild and easy-handle conditions,3-chlorooxindoles was introduced to react with the o-QMs, which were synthesized in situ from 2-(1-tosylalkyl) phenols. And the optimized target products were obtained through condition selection. The gram-scale experiments were conducted to verify the practicality of this method. The results show that under optimized condition, the yield of target product can achieve 92% and the diastereoselectivity dr is more than 20:1. And high yield and diastereoselectivity can be maintained when the substrate amount increases. The method can be applied widely and multiple compounds such as 2-(1-tosylalkyl) phenols and 3-chlorooxindoles can be used as materials in this method.

 

Key words: 3-chlorooxindole; ortho-quinone methides; Michael addition/cyclizaiton; spirooxindoles

中南大学学报(自然科学版)
  ISSN 1672-7207
CN 43-1426/N
ZDXZAC
中南大学学报(英文版)
  ISSN 2095-2899
CN 43-1516/TB
JCSTFT
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