3-甲酰基色酮与异硫氰基氧吲哚的Michael/环化串联反应
Michael/Cyclization Tandem Reaction of 3-Formylchromones with Isothiocyanatooxindoles
杜大明 1耿雪洋1
作者信息
- 1. 北京理工大学 化学与化工学院 医药分子科学与制剂工程工业和信息化部重点实验室,北京 100081
- 折叠
摘要
多环色满酮化合物作为多种天然产物和药物分子的核心结构,具有抗癌、抗炎、抗菌和神经保护等多种药理活性,因而吸引了众多有机化学家的关注.由色酮衍生物构建色满酮化合物能够在进一步丰富色满酮结构分子库的同时填补相关色酮化合物研究方面的空白.利用 3-甲酰基色酮和 3-异硫氰基氧吲哚的Michael/环化串联反应,能够以较高的产率(高达 92%)和优异的非对映选择性(高达＞20:1 dr)得到相应的螺杂环产物.通过该反应成功构建了一系列的具有 3个连续立体中心,并且含有一个 4取代碳的吡咯烷基螺环氧吲哚-色满酮类化合物,同时对该反应的不对称催化反应条件也进行了初步探索.
Abstract
As the core structure of a variety of natural products and drug molecules,polycyclic chromanone com-pounds possess many pharmacological activities such as anticancer,anti-inflammatory,antibacterial and neuro-protective,so they have attracted the attention of many organic chemists.The construction of chromanone com-pounds based on chromone derivatives can further enrich the molecular library of chromanone structure,filling the research gap on chromone compounds.In this paper,a Michael/cyclization tandem reaction was carried out with 3-formylchromones and 3-isothiocyanatooxindoles to produce the corresponding spirocyclic heterocycles with high yields(up to 92%)and excellent diastereoselectivities(up to＞20:1 dr).Based on the reaction,a series of pyrrolidinyl spirooxindole-chromanones with three continuous stereocenters and a tetrasubstituted carbon were successfully constructed,and some asymmetric catalytic reaction conditions of the reaction were also pre-liminarily explored.
关键词
有机合成/不对称催化/色酮/方酰胺/3-异硫氰基氧吲哚/螺杂环化合物Key words
organic synthesis/asymmetric catalysis/chromone/squaramide/3-isothiocyanatooxindole/spiro-cyclic heterocycle引用本文复制引用
出版年
2025
NETL
NSTL
万方数据