磺酰腙的高效快速合成及其抗菌性能初探——推荐一个医学本科院校化学创新实验

doi:10.3866/PKU.DXHX202309091

Abstract

Abstract:

In the teaching process of the organic chemistry experiment, the content typically involves the synthesis or extraction of a certain compound, often lacking in structural identification and property testing of the target compound. To improve the quality of organic chemistry experimental teaching, and cultivate students' scientific research literacy and innovation ability, commercially available aldehydes, ketones and p-toluenesulfonyl hydrazide are used as reactants. N-tosylhydrazone derivatives were effectively synthesized within 1 min under solvent-free conditions by using a grinding method at room temperature, and the structure and properties of the products were also studied. Compounds 3i and 3h have the best inhibitory effect against Escherichia coli during antibacterial experimental research. The experiment, encompassing synthesis, TLC detection, and column chromatography operations, serves to hone students' operational skills in organic compound synthesis, purification, and structural identification. Students are required to consult literature independently and proficiently utilize software tools like Origin, ChemDraw and MestRec, which fosters their ability to analyze and resolve problems. This improved experimental framework, aimed at elevating students' comprehensive qualities, is well-suited for the foundational organic chemistry experimental teaching.

Key words: Solvent-free conditions, Tosylhydrazones, Grinding method, Antibacterial properties

Jingjie Tang, Luying Xie, Jiayu Liu, Shangyu Shi, Xinyu Sun, Jiayang Lin, Qikun Yang, Chuan'ang Yu, Zecheng Wang, Yingying Wang, Zengyang Xie. Efficient Rapid Synthesis and Antibacterial Activities of Tosylhydrazones: A Recommended Innovative Chemistry Experiment for Undergraduate Medical University[J].University Chemistry, 2024, 39(3): 316-326.

Figures/Tables 11

References 13

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Entry	溶剂	反应方式(温度)	时间	产率(%) ^b
1	乙醇	常规搅拌(室温)	1.5 h	85
2	乙酸乙酯	常规搅拌(室温)	1.5 h	82
3	乙腈	常规搅拌(室温)	1.5 h	87
4	四氢呋喃	常规搅拌(室温)	1.5 h	72
5	甲苯	常规搅拌(室温)	1.5 h	77
6	氯仿	常规搅拌(室温)	1.5 h	81
7	N, N-二甲基甲酰胺	常规搅拌(室温)	1.5 h	68
8	乙腈	常规搅拌(90 ℃)	30 min	88
9	– ^c	研磨(室温)	1 min	93
10	– ^c	研磨(室温)	6 min	93
11	– ^c	研磨(室温)	10 min	93

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Efficient Rapid Synthesis and Antibacterial Activities of Tosylhydrazones: A Recommended Innovative Chemistry Experiment for Undergraduate Medical University

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