Cyclization of N-(2-Ethynylphenyl)acrylamides for the Synthesis of Heteropolycyclic Compounds

doi:10.6023/cjoc202409034

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (10): 3741-3754.DOI: 10.6023/cjoc202409034 Previous Articles Next Articles

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N-(2-乙炔基苯基)丙烯酰胺的环化反应用于杂多环化合物的合成

董道青^a, 王怡萌^a, 朱耕宁^a, 王艳丽^a, 于曙光^a, 刘娟^b, 冯健新^c, 徐鑫明^d^,^*(), 颜世强^e^,^*(), 王祖利^a^,^*()

^a 青岛农业大学化学与药学院山东青岛 266109
^b 青岛三人行化学有限公司山东青岛 266045
^c 威海海洋职业学院山东威海 264000
^d 烟台大学化学化工学院山东烟台 264005
^e 山东达因海洋生物制药股份有限公司山东威海 264300

收稿日期:2024-09-25 修回日期:2024-10-30 发布日期:2024-12-12
基金资助:
威海市医用调理功能食品加工技术重点实验室2024年度科研开放专项资金(WHYY20240006); 青岛农业大学中青年教师访学项目(2024); 青岛农业大学普通教学改革研究项目(XJY2024063); 青岛农业大学思想政治教育研究课题研究成果(QNSZ2025023)

Cyclization of N-(2-Ethynylphenyl)acrylamides for the Synthesis of Heteropolycyclic Compounds

Daoqing Dong^a, Yimeng Wang^a, Gengning Zhu^a, Yanli Wang^a, Shuguang Yu^a, Juan Liu^b, Jianxin Feng^c, Xinming Xu^d^,^*(), Shiqiang Yan^e^,^*(), Zuli Wang^a^,^*()

^a College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao, Shandong 266109
^b Qingdao Sanrenxing Chemistry Co., Ltd., Qingdao, Shandong 266045
^c Weihai Ocean Vocational College, Weihai, Shandong 264000
^d College of Chemistry and Chemical Engineering, Yantai University, Yantai, Shandong 264005
^e Shandong Dyne Marine Biopharmaceutical Co., Ltd., Weihai, Shandong 264300

Received:2024-09-25 Revised:2024-10-30 Published:2024-12-12
Contact: * xuxm18@ytu.edu.cn; 16937924@qq.com; wangzulichem@163.com
Supported by:
Special Fund Project for Scientific Research Openness of the Key Laboratory of Medical Conditioning Functional Food Processing Technology in Weihai City(WHYY20240006); Mid-Young Teachers Visiting Program of Qingdao Agricultural University(2024); General Education Reform and Research Project of Qingdao Agricultural University(XJY2024063); Research Results of the Ideological and Political Education Research Project of Qingdao Agricultural University(QNSZ2025023)

N-(2-Ethynylphenyl)acrylamides have emerged as key intermediates for the synthesis of complex heteropolycyclic compounds. The recent advances focus on the tandem cyclization involving these precursors, among which formation of fused six/N-three, six/five (N, S, O), and six/six-membered rings are highlighted. Nitrogen, sulfur, and oxygen incorporations into five-membered rings provide efficient routes to bioactive polycyclic molecules. These cyclization reactions exhibit excellent atom economy, high efficiency, and good functional group compatibility. Furthermore, novel catalytic systems and photochemical strategies also expand the synthetic applications of these precursors. Taken together, these advancements offer versatile tools for the synthesis of intricate heterocyclic scaffolds with broad applications in organic and medicinal chemistry.

Key words: cyclization, heteropolycyclic compounds, N-(2-ethynylphenyl)acrylamides, radical, visible light

Cite this article

Daoqing Dong, Yimeng Wang, Gengning Zhu, Yanli Wang, Shuguang Yu, Juan Liu, Jianxin Feng, Xinming Xu, Shiqiang Yan, Zuli Wang. Cyclization of N-(2-Ethynylphenyl)acrylamides for the Synthesis of Heteropolycyclic Compounds[J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3741-3754.

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Fig. & Tab. 15

Scheme 1. General method for the synthesis of N-(2-ethynyl- phenyl)acrylamides

Scheme 2. CF3 radical cascade cyclization of compound 2A with Togni’s reagent

Scheme 3. Copper-catalyzed sequential trifluoromethylation and rearrangement of N-(2-ethynylphenyl)acrylamides

Scheme 4. One-pot synthesis of the pyrrolo[2-de]quinolinone with t-BuONO and H2O

Scheme 5. Copper-catalyzed radical [2＋2＋1] annulation of 1,n-enynes with azidobenziodoxolone

Scheme 6. Cyclization reaction between N-(2-ethynylphenyl)- acrylamides and TMSN3

Scheme 7. Copper-catalyzed cascade cyclization of 1,7-enynes with metal sulfides

Scheme 8. Oxidative [2＋2＋1] heteroannulation of 1,7-enynes with disulfanes, facilitated by Et3N

Scheme 9. Photocatalytic synthesis of thieno[3,4-c]quinolin-4(5H)-ones/selenopheno[3,4-c]quinolin-4(5H)-ones

Scheme 10. Synthesis of thieno[3,4-c]quinolin-4(5H)ones from 1,7-enynes and thiocyanates

Scheme 11. Cascade reactions assisted by microwaves for the synthesis of 2-quinolinone-fused γ-lactones

Scheme 12. Iron-catalyzed radical annulation of benzene-linked 1,7-enynes with aldehydes

Scheme 13. Visible-light-mediated cascade cyclization of benzene-linked 1,7-enynes with benzoyl chlorides

Scheme 14. Reaction of N-methyl-N-(2-ethynylphenyl)methacrylamide with triazine esters

Scheme 15. Reaction of N-methyl-N-(2-(phenylethynyl)phenyl)methacrylamide with triazine esters

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N-(2-乙炔基苯基)丙烯酰胺的环化反应用于杂多环化合物的合成

Cyclization of N-(2-Ethynylphenyl)acrylamides for the Synthesis of Heteropolycyclic Compounds

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Fig. & Tab. 15

References 22

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