钯催化4-乙烯基苯并噁嗪酮和茚-2-甲醛串联环化反应—

引用本文: 张茜苑, 董锐, 杨洋, 丁佳鹏, 苗志伟. 钯催化4-乙烯基苯并噁嗪酮和茚-2-甲醛串联环化反应——介绍一个有机化学综合实验[J]. 大学化学, 2025, 40(9): 361-367. doi: 10.12461/PKU.DXHX202410062 shu

Citation: 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[J]. University Chemistry, 2025, 40(9): 361-367. doi: 10.12461/PKU.DXHX202410062 shu

钯催化4-乙烯基苯并噁嗪酮和茚-2-甲醛串联环化反应——介绍一个有机化学综合实验

南开大学化学学院, 元素有机化学国家重点实验室, 天津 300071

通讯作者: 苗志伟,E-mail:miaozhiwei@nankai.edu.cn

基金项目:
国家自然科学基金面上项目(22071113)；福建省南平市科技项目(N2020Z008)；南开大学沧州渤海新区绿色化工研究院基金项目(NCC2020FH01)

摘要: 有机化学综合实验是化学教育中不可或缺的一环，它不仅能够显著提高本科生的基本实验技能，而且有助于加深本科生对专业知识的理解和掌握，为未来的学术探索和职业生涯奠定坚实的基础。本文介绍了一个有机化学综合实验，以茚-2-甲醛和4-乙烯基苯并噁嗪酮为反应物，利用钯催化串联环化反应合成12-乙烯基-7,12-二氢苯并[双]茚并[1,2-e]氮杂卓化合物，并且使用高分辨质谱(HRMS)、核磁共振氢谱(1H NMR)和碳谱(¹³C NMR)等技术手段对产物结构进行表征。

关键词:

English

Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment

State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China

Corresponding author: Zhiwei Miao, miaozhiwei@nankai.edu.cn

Received Date: 21 October 2024
Accepted Date: 16 January 2025
Available Online: 22 May 2025

Abstract: Comprehensive organic chemistry experiments constitute a fundamental component of chemical education, serving to significantly enhance undergraduates’ basic laboratory skills while deepening their understanding of specialized knowledge. This foundation proves crucial for future academic pursuits and professional development. We present herein an integrated organic chemistry experiment involving the palladium-catalyzed tandem cyclization of 4-vinylbenzoxazinone and indene-2-carbaldehyde to synthesize 12-vinyl-7,12-dihydrobenzo[b]indeno[1,2-e]azepine. The product structure was characterized using high-resolution mass spectrometry (HRMS), along with ¹H and ¹³C nuclear magnetic resonance spectroscopy.

Key words:

Comprehensive organic chemistry experiment
/ Tandem cyclization
/ Palladium catalysis
/ Synthesis and structural characterization

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钯催化4-乙烯基苯并噁嗪酮和茚-2-甲醛串联环化反应——介绍一个有机化学综合实验

通讯作者: 苗志伟,E-mail:miaozhiwei@nankai.edu.cn

English

Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment

Corresponding author: Zhiwei Miao, miaozhiwei@nankai.edu.cn

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

钯催化4-乙烯基苯并噁嗪酮和茚-2-甲醛串联环化反应——介绍一个有机化学综合实验

通讯作者: 苗志伟,E-mail:miaozhiwei@nankai.edu.cn

English

Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment

Corresponding author: Zhiwei Miao, miaozhiwei@nankai.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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