Simple Synthesis of Arylamines from Tetraynes via the Hexadehydro-Diels-Alder Reaction

doi:10.6023/cjoc201409032

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (3): 724-730.DOI: 10.6023/cjoc201409032 Previous Articles Next Articles

ARTICLE

四炔的芳炔环加成反应简便合成芳胺

吴玉芹^a, 于凉云^a, 张奇^a, 李立冬^a,b

a 盐城工学院化学与生物工程学院盐城 224051;
b 安徽师范大学化学与材料科学学院芜湖 241000

收稿日期:2014-09-20 修回日期:2014-10-15 发布日期:2014-11-07
通讯作者: 李立冬 E-mail:ld-l@163.com
基金资助:
国家自然科学基金(No. 21272005)资助项目.

Simple Synthesis of Arylamines from Tetraynes via the Hexadehydro-Diels-Alder Reaction

Wu Yuqin^a, Yu Liangyun^a, Zhang Qi^a, Li Lidong^a,b

a School of Chemical and Biological Engineering, Yancheng Institute of Technology, Yancheng 224051;
b College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000

Received:2014-09-20 Revised:2014-10-15 Published:2014-11-07
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21272005).

1. Simple Synthesis of Arylamines from Tetraynes via the Hexadehydro-Diels-Alder Reaction.PDF(513KB)

Abstract

Arylamines are widespread in natural products, pharmaceuticals and molecular materials, and are useful synthetic building blocks. From a synthetic standpoint, the formation of C_aryl—N bonds has been achieved by classical methods such as nucleophilic aromatic substitution, electrophilic nitration/reduction, or the transition-metal-mediated arylation of amides. This paper describes an efficient method for the synthesis of arylamines by the hexadehydro-Diels-Alder (HDDA) reaction of tetraynes under catalyst-free condition. This process is achieved in the absence of metal catalyst, base or oxidant, and it does not require the pre-installation of directing groups. This reaction exhibited an excellent regioselectivity, producing highly substituted fused yne-functionalized bicyclic compounds under mild conditions with good to excellent yields. All new products were fully characterized by various spectroscopic techniques and high-resolution mass spectrometry. The molecular structure of 3h was confirmed using single-crystal X-ray analyses.

Key words: arylamines, synthesis, C_aryl—N coupling, HDDA reaction

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Wu Yuqin, Yu Liangyun, Zhang Qi, Li Lidong. Simple Synthesis of Arylamines from Tetraynes via the Hexadehydro-Diels-Alder Reaction[J]. Chin. J. Org. Chem., 2015, 35(3): 724-730.

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四炔的芳炔环加成反应简便合成芳胺

Simple Synthesis of Arylamines from Tetraynes via the Hexadehydro-Diels-Alder Reaction

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