Home

Citation: Yinuo Wang, Ziyu Liu, Hongxia Tan, Jun Tong, Dazhen Xu. Synthesis of Bromobenzoxazine: Introduce a Comprehensive Organic Chemistry Experiment Transformed from Undergraduate Research Innovation[J]. University Chemistry, ;2025, 40(10): 208-216. doi: 10.12461/PKU.DXHX202411077 shu

Synthesis of Bromobenzoxazine: Introduce a Comprehensive Organic Chemistry Experiment Transformed from Undergraduate Research Innovation

National Engineering Research Center of Pesticide, College of Chemistry, Nankai University, Tianjin 300071, China

Received Date: 28 November 2024
Revised Date: 3 April 2025

This article introduces a comprehensive organic chemistry experiment originated from undergraduate scientific research training program. Using 2-aminoacetophenone as the starting material, the experiment demonstrates the synthesis of benzoxazine through a three-step sequence involving Wittig reaction, amidation, and bromocyclization. Two intermediates and the final product were characterized and analyzed for their structures. The experiment included techniques such as heating reflux, thin-layer chromatography (TLC) detection, filtration, and column chromatography, all designed to enhance students’ skills in multi-step organic compound synthesis and spectral analysis. In addition, the experiment incorporates both classical and current scientific organic methods, which not only helps students to consolidate their theoretical knowledge, improve their experimental ability, but also stimulate their interest in learning and exploring chemistry.
- Wittig reaction,
- Amidation,
- Iron salt catalysis,
- Cyclization reaction,
- Organic synthesis
1. [1]
  Krantz, A.; Spencer, R. W.; Tam, T. F.; Liak, T. J.; Copp, L. J.; Thomas, E. M.; Rafferty, S. P. J. Med. Chem. 1990, 33, 464.
2. [2]
  Hays, S. J.; Caprathe, B. W.; Gilmore, J. L.; Amin, N.; Emmerling, M. R.; Michael, W.; Nadimpalli, R.; Nath, R.; Raser, K. J.; Stafford, D.; et al. J. Med. Chem. 1998, 41, 1060.
3. [3]
  Zhang, P.; Terefenko, E. A.; Fensome, A.; Zhang, Z.; Zhu, Y.; Cohen, J.; Winneker, R.; Wrobel, J.; Yardley, J. Bioorg. Med. Chem. Lett. 2002, 12, 787.
4. [4]
  Hiroshi, S.; Keizo, H.; Yoshikazu, K.; Masaki, T.; Masanori, O. 4H-3,1-Benzoxazine Derivatives and Agricultural or Horticultural Fungicide Containing Them. EP120480A1, 1984-10-03.
5. [5]
  Kobzina, J. W. Herbicidal N-haloacetyl-1,2-dihydro-4H-3,1-benzoxazines. US4030906A, 1976-04-08.
6. [6]
  Djabrouhou, N.; Guermouche M-H. J. Pharm. Biomed. Anal. 2014, 100, 11.
7. [7]
  Fenton, G.; Newton, C. G.; Wyman, B. M.; Bagge, P.; Dron, D. I.; Riddell, D.; Jones, G. D. J. Med. Chem. 1989, 32, 265.
8. [8]
9. [9]
  Zhao, T.-T.; Bian, Q.; Zhao, Y.-W.; Xu, L.-L.; Xu, D.-Z.; Zhao, W.-G. Synthesis 2024, 56, 2993.
10. [10]
  Wang, Z.-L.; Zhang, Y.-H.; Huang, J.-Y.; Zhou, J.; Yu, Y.-Q.; Feng, D.; Xu, D.-Z. Green Chem. 2023, 25, 4463.
11. [11]
1. [1]
  Zhi Chai , Huashan Huang , Xukai Shi , Yujing Lan , Zhentao Yuan , Hong Yan . Wittig反应的立体选择性. University Chemistry, 2025, 40(8): 192-201. doi: 10.12461/PKU.DXHX202410046
2. [2]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
3. [3]
  Fengxiao Wang , Zhiwei Miao , Yaofeng Yuan . 有机磷化学与化学教学. University Chemistry, 2025, 40(8): 158-168. doi: 10.12461/PKU.DXHX202410077
4. [4]
  Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
5. [5]
  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
6. [6]
  Shuhui Li , Rongxiuyuan Huang , Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028
7. [7]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
8. [8]
  Yansong Xiao , Yi Huang , Xingxing Ma , Qiuling Song . The Matteson Reaction in Organic Synthesis: From Fundamentals to Frontiers. University Chemistry, 2025, 40(10): 114-120. doi: 10.12461/PKU.DXHX202411023
9. [9]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
10. [10]
  Xiyuan Zhang , Rui Dong , Yang Yang , Jiapeng Ding , Zhiwei Miao . Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(9): 361-367. doi: 10.12461/PKU.DXHX202410062
11. [11]
  Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
12. [12]
  Yan Qi , Yueqin Yu , Weisi Guo , Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021
13. [13]
  Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046
14. [14]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
15. [15]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . Insights into the development of 2D covalent organic frameworks as photocatalysts in organic synthesis. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-0. doi: 10.1016/j.actphy.2025.100086
16. [16]
  Wenjie SHI , Fan LU , Mengwei CHEN , Jin WANG , Yingfeng HAN . Synthesis and host-guest properties of imidazolium-functionalized zirconium metal-organic cage. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 105-113. doi: 10.11862/CJIC.20240360
17. [17]
  Zihao Guo , Shichen Ma , Kin Shing Chan . 烯烃环化反应中6电子试剂的等瓣相似性和等电子关系. University Chemistry, 2025, 40(6): 160-166. doi: 10.12461/PKU.DXHX202408038
18. [18]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
19. [19]
  Linlin Wu , Yonghua Zhou , Zhongbei Li , Liu Deng , Younian Liu , Limiao Chen , Jianhan Huang . Digital Education Promoting Applied Chemistry Comprehensive Experiments: A Case Study of Catalytic Oxidation of Hydrogen Chloride and Reaction Kinetics. University Chemistry, 2025, 40(9): 273-278. doi: 10.12461/PKU.DXHX202411018
20. [20]
  Houjin Li , Wenjian Lan . Name Reactions in University Organic Chemistry Laboratory. University Chemistry, 2024, 39(4): 268-279. doi: 10.3866/PKU.DXHX202310016

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(83)
HTML views(11)

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