炔醇分子内环化促发的串联反应在螺杂环化合物合成中的应用

doi:10.6023/cjoc202006050

有机化学 ›› 2021, Vol. 41 ›› Issue (2): 582-593.DOI: 10.6023/cjoc202006050 上一篇下一篇

综述与进展

炔醇分子内环化促发的串联反应在螺杂环化合物合成中的应用

余述燕^a^,^*(), 高丽宏^a, 闫溢哲^b, 尹志刚^a, 商永嘉^c^,^*()

a 郑州轻工业大学材料与化学工程学院郑州 450002
b 郑州轻工业大学食品与生物工程学院郑州 450002
c 安徽师范大学功能分子固体教育部重点实验室安徽芜湖 240001

收稿日期:2020-06-23 修回日期:2020-07-28 发布日期:2020-08-19
通讯作者: 余述燕, 商永嘉
作者简介:
* Corresponding authors. E-mail: yushuyan_zzuli@163.com; shyj@mail.ahnu.edu.cn
基金资助:
国家自然科学基金(21602207); 郑州轻工业大学博士科研基金(2014BSJJ009); 郑州轻工业大学青年骨干教师(2019XGGJS010)

Application of Cascade Reactions in the Synthesis of Sprio-hetero- cycles Initiated by Intramolecular Cyclization of Alkynols

Shuyan Yu^a^,^*(), Lihong Gao^a, Yizhe Yan^b, Zhigang Yin^a, Yongjia Shang^c^,^*()

a College of Material and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002
b College of Food and Bioengineering, Zhengzhou University of Light Industry, Zhengzhou 450002
c Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000

Received:2020-06-23 Revised:2020-07-28 Published:2020-08-19
Contact: Shuyan Yu, Yongjia Shang
Supported by:
the National Natural Science Foundation of China(21602207); the Doctoral Research Fund of Zhengzhou University of Light Industry(2014BSJJ009); the Young Backbone Teachers’ Fund of Zhengzhou University of Light Industry(2019XGGJS010)

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摘要/Abstract

螺杂环化合物独特的立体结构和丰富的理化特性, 激发了研究工作者对其高效合成方法的持续关注. 炔醇在过渡金属作用下经exo-dig式分子内环化可原位形成环外烯醇醚, 其作为一类高活性的C2合成子, 能够与同时具有亲电和亲核特性的“双亲性底物”发生串联反应, 实现螺杂环骨架的快速构建. 综述了近年来炔醇分子内环化促发的串联反应在螺杂环化合物合成中的应用进展, 以期激发更多相关研究工作的设计与报道. 按照参与螺环构建的“双亲性底物”原子数目的不同进行分类, 重点阐述了反应采用的催化体系和反应机制, 分析了目前该领域存在的挑战, 并对未来的发展进行了展望.

关键词: 螺杂环, 炔醇, 串联反应, 环外烯醇醚

Due to their unique stereoscopic structure and rich physical and chemical properties, spiro heterocyclic compounds have aroused the continuous attention of researchers on their efficient synthesis methods. The exo-cyclic enol ethers generated in situ by exo-dig cyclization of alkynols under the promotion of transition metals could serve as C2 synthons to react with various "amphiphilic substrates" through cascade reactions mode. These cascade reactions could afford spiro heterocyclic skeletons in highly efficient and direct manners. In this paper, the application progress of cascade reactions in the synthesis of sprio-heterocycles initiated by intramolecular cyclization of alkynols is reviewed, which aims to stimulate the disclosure of more related research work. These work is elaborated according to the different atom numbers of the "amphiphilic substrates" involved in the construction of the spiro framworks. The catalytic system and reaction mechanism are mainly described, the challenges in this field are analyzed, and the future development is also put forward.

Key words: sprio-heterocycles, alkynols, cascade reactions, exo-cyclic enol ether

引用此文

余述燕, 高丽宏, 闫溢哲, 尹志刚, 商永嘉. 炔醇分子内环化促发的串联反应在螺杂环化合物合成中的应用[J]. 有机化学, 2021, 41(2): 582-593.

Shuyan Yu, Lihong Gao, Yizhe Yan, Zhigang Yin, Yongjia Shang. Application of Cascade Reactions in the Synthesis of Sprio-hetero- cycles Initiated by Intramolecular Cyclization of Alkynols[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 582-593.

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图/表 21

图式1. 一些具有螺杂环骨架的药物

Figure 1. Some drugs containing spiroheterocycle skeletons

图式2. 螺环化合物的主要合成方法

Scheme 2. Synthetic methods for spirocycles

图式3. 炔醇分子内环化促发的串联反应原理

Scheme 3. Mechanism of cascade reactions involving intramolecular cyclization of alkynols

图式4. 炔醇、醛和芳胺的三组分反应

Scheme 4. Three-component reaction of alkynol, aldehyde and aromatic aniline

图式5. 炔醇和高炔丙胺的串联反应

Scheme 5. Cascade reaction of alkynol and homopropargylamine

图式6. 炔醇、水杨醛和芳胺(或原甲酸酯)的三组分反应

Scheme 6. Three-component reaction of alkynol, salicylaldehyde and aromatic aniline (ortho formate)

图式7. 炔醇与不饱和酮酸酯的串联反应

Scheme 7. Cascade reaction of alkynol and unsaturated keto- esters

图式8. 炔醇与邻羟基苄醇的串联反应

Scheme 8. Cascade reaction of alkynol and o-quinone methide

图式9. 炔醇与多种亚甲基苯醌的串联反应

Scheme 9. Cascade reaction of alkynol and quinone methides

图式10. 炔醇与水杨醛的串联反应

Scheme 10. Cascade reaction of alkynol and salicylaldehyde

图式11. 炔醇和邻炔基水杨醛的串联反

Scheme 11. Cascade reaction of alkynol and ortho-alky- nylsalicylaldehyde

图式12. 炔醇、醛和尿素(硫脲)的三组分反应

Scheme 12. Three-component reaction of alkynol, aldehyde and urea (thioure a)

图式13. 炔醇、胺与乙醛酸的三组分反应

Scheme 13. Three-component reaction of alkynol, aniline and glyoxylic acid

图式14. 炔醇与酮酯的串联反应

Scheme 14. Cascade reaction of alkynol and keto-ester

图式15. 炔醇与苯醌单亚胺的串联反应

Scheme 15. Cascade reaction of alkynols and quinone mo-noimines

图式16. 炔醇与氮杂环丙烷的串联反应

Scheme 16. Cascade reaction of alkynols and aziridines

图式17. 炔醇、醛(酮)和肼的三组分反应

Scheme 17. Three-component reaction of alkynol, aldehyde (ketone) and hydrazine

图式18. 炔醇与丙二烯基硅醚的串联反应

Scheme 18. Cascade reaction of alkynol and propadienyl silyl ethers

图式19. 炔醇与共轭烯炔酮的串联反应

Scheme 19. Cascade reaction of alkynols and alkynyl enones

图式20. 环外己烯醇醚中间体参与的反应

Scheme 20. Reaction involving cyclohexene alcohol ether intermediate

图式21. 4-戊炔-1-醇、苯甲醛和苯胺的三组分反应

Scheme 21. Three-component reaction of 4-pentyne-1-ol, benzaldehyde and aniline

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炔醇分子内环化促发的串联反应在螺杂环化合物合成中的应用

Application of Cascade Reactions in the Synthesis of Sprio-hetero- cycles Initiated by Intramolecular Cyclization of Alkynols

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