Home

Citation: Yicheng Luo, Yanfeng Gao, Weisheng Lin, Zhiwei Miao. Synthesis of Diethyl 2-Benzyl-3,4-dioxo-6-phenyl-9-vinyl-2-azaspiro [4.4]nonane-7,7-dicarboxylate through Palladium Catalyzed Tandem Cyclization: Introducing a Comprehensive Experiment of Organic Chemistry[J]. University Chemistry, ;2023, 38(10): 250-257. doi: 10.3866/PKU.DXHX202212063 shu

Synthesis of Diethyl 2-Benzyl-3,4-dioxo-6-phenyl-9-vinyl-2-azaspiro [4.4]nonane-7,7-dicarboxylate through Palladium Catalyzed Tandem Cyclization: Introducing a Comprehensive Experiment of Organic Chemistry

1.
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China;
2.
Department of Ecological and Resources Engineering, Wuyi University, Wuyishan 354300, Fujian Province, China

Corresponding author: Zhiwei Miao, miaozhiwei@nankai.edu.cn
Received Date: 23 December 2022
Revised Date: 7 March 2023

The comprehensive experiment of organic chemistry is conducive to training students’ experimental skills, cultivating their innovative ability, and stimulating their independent thinking ability and research consciousness. This article presents a comprehensive organic chemistry experiment in which 2-vinylcyclopropane-1,1-diethyl diformate and 1-benzyl-4-benzylidene-2,3-pyrrolidone were used as reactants to synthesize 2-benzyl-3,4-dicarbonyl-6-phenyl-9-vinyl-2-azanone-7,7-dicarboxylate ethyl ester by palladium-catalyzed tandem cyclization reaction. ¹H NMR, ¹³C NMR and HRMS characterized the structure of the product.
1. [1]
2. [2]
3. [3]
4. [4]
  Wan, M. C.; Rui, S. ACS Catal. 2020, 10, 9170.
5. [5]
  Southwick, P. L.; Barnas, E. F. J. Org. Chem. 1962, 27, 98.
6. [6]
  Huang, X. B.; Li, X. J.; Li, T. T.; Chen, B.; Chu, W. D.; He, L.; Liu, Q. Z. Org. Lett. 2019, 21, 1713.
7. [7]
  Badiola, E.; Olaizola, I.; Vazquez, A.; Vera, S.; Mielgo, A.; Palomo, C. Chem. Eur. J. 2017, 23, 8185.
8. [8]
  Cheng, Q.; Xie, J. H.; Weng, Y, C.; You, S. L. Angew. Chem. Int. Ed. 2019, 58, 5739.
1. [1]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
2. [2]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
3. [3]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
4. [4]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
5. [5]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
6. [6]
  Houjin Li , Wenjian Lan . Name Reactions in University Organic Chemistry Laboratory. University Chemistry, 2024, 39(4): 268-279. doi: 10.3866/PKU.DXHX202310016
7. [7]
  Gang Liu , Heng Zhang , Ying Ma , Shiling Yuan , Qisheng Song , Zhenghu Xu , Jichao Sun . Exploration and Practice on Improving the Teaching Quality of Organic Chemistry Laboratory Course. University Chemistry, 2024, 39(4): 70-74. doi: 10.3866/PKU.DXHX202309079
8. [8]
  Daojuan Cheng , Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105
9. [9]
  Mengchen Liao , Hua Yang , Younian Liu , Zhen He , Maolin Zhang , Qing Liu , Jiwen Ding . Exploration and Implementation of Refined Management Practices in Basic Organic Chemistry Laboratories. University Chemistry, 2024, 39(10): 164-173. doi: 10.3866/PKU.DXHX202403041
10. [10]
  Weihua Jiang , Yongsheng Zhou , Qiaoqiao Teng . Progressive Teaching Model in the Practice and Exploration of Ideological and Political Education in Laboratory Courses: Taking the Organic Chemistry Experiment “Synthesis of Aspirin” as an Example. University Chemistry, 2024, 39(2): 99-104. doi: 10.3866/PKU.DXHX202306028
11. [11]
  Jian Jin , Jing Cheng , Xueping Yang . Integration Practice of Organic Chemistry Experiment and Safety Education: Taking the Synthesis of Triphenylmethanol as an Example. University Chemistry, 2024, 39(3): 345-350. doi: 10.3866/PKU.DXHX202309010
12. [12]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
13. [13]
  Fuxian Wan , Ying Li , Yuanhong Zhang , Shuhua Zhu , Jing Xu , Yanfang Wang , Lili Zhang . Exploration and Practice of Teaching in Agricultural Characteristic Organic Chemistry Course. University Chemistry, 2024, 39(2): 298-306. doi: 10.3866/PKU.DXHX202308041
14. [14]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
15. [15]
  Biaolin Yin , Yuanfu Deng , Dongen Lin . Exploration and Practice of Integrating Ideological and Political Education and Innovative Thinking into “Organic Chemistry” Teaching. University Chemistry, 2024, 39(2): 286-291. doi: 10.3866/PKU.DXHX202308026
16. [16]
  Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081
17. [17]
  Fei Xie , Shichong Yu , Ting Wang , Yongsheng Jin , Dazhi Zhang , Yumeng Hao . Practice and Exploration of O-PIRTAS Flipped Classroom in Organic Chemistry Course. University Chemistry, 2024, 39(4): 238-243. doi: 10.3866/PKU.DXHX202310055
18. [18]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
19. [19]
  Renqing Lü , Shutao Wang , Fang Wang , Guoping Shen . Computational Chemistry Aided Organic Chemistry Teaching: A Case of Comparison of Basicity and Stability of Diazine Isomers. University Chemistry, 2025, 40(3): 76-82. doi: 10.12461/PKU.DXHX202404119
20. [20]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(415)
HTML views(34)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return