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

doi:10.6023/cjoc202006050

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 582-593.DOI: 10.6023/cjoc202006050 Previous Articles Next Articles

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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

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)

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

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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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Fig. & Tab. 21

Figure 1. Some drugs containing spiroheterocycle skeletons

Scheme 2. Synthetic methods for spirocycles

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

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

Scheme 5. Cascade reaction of alkynol and homopropargylamine

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

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

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

Scheme 9. Cascade reaction of alkynol and quinone methides

Scheme 10. Cascade reaction of alkynol and salicylaldehyde

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

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

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

Scheme 14. Cascade reaction of alkynol and keto-ester

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

Scheme 16. Cascade reaction of alkynols and aziridines

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

Scheme 18. Cascade reaction of alkynol and propadienyl silyl ethers

Scheme 19. Cascade reaction of alkynols and alkynyl enones

Scheme 20. Reaction involving cyclohexene alcohol ether intermediate

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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