大学化学 >> 2025, Vol. 40 >> Issue (10): 208-216.doi: 10.12461/PKU.DXHX202411077

化学实验 上一篇    下一篇

溴代苯并噁嗪的合成——推荐一个由本科科研创新转化的综合有机化学实验

王一诺, 刘子羽, 谭红霞, 童军, 徐大振   

  1. 南开大学化学学院, 农药国家工程研究中心, 天津 300071
  • 收稿日期:2024-11-28 录用日期:2025-04-03 发布日期:2025-09-17
  • 通讯作者: 童军, 徐大振 E-mail:xudazhen@nankai.edu.cn;tongjun@nankai.edu.cn
  • 基金资助:
    国家级大学生创新创业训练计划(202310055078, 202410055075)

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

Yinuo Wang, Ziyu Liu, Hongxia Tan, Jun Tong, Dazhen Xu   

  1. National Engineering Research Center of Pesticide, College of Chemistry, Nankai University, Tianjin 300071, China
  • Received:2024-11-28 Accepted:2025-04-03 Published:2025-09-17
  • Contact: Jun Tong, Dazhen Xu E-mail:xudazhen@nankai.edu.cn;tongjun@nankai.edu.cn

摘要: 本文介绍了一个源于本科生科研训练计划的综合有机化学实验。该实验以2-氨基苯乙酮为原料,通过Wittig、酰胺化和溴环化三步反应实现对苯并噁嗪的制备。该实验中,两个中间体和最终产物都进行了结构表征和分析,涉及的主要操作包括:加热回流、薄层色谱检测、过滤和柱色谱等技术,旨在提高学生有机化合物多步合成及波谱解析能力。此外,经典和最新报道的有机合成方法都涉及其中,这不仅有助于学生巩固理论知识、提高实验能力,还能激发他们学习探索化学的兴趣。

关键词: Wittig反应, 酰胺化, 铁盐催化, 环化反应, 有机合成

Abstract: 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.

Key words: Wittig reaction, Amidation, Iron salt catalysis, Cyclization reaction, Organic synthesis