An unexpected tetracyclic product isolated during the synthesis of biscoumarins catalyzed by [MIM(CH2)4SO3H][HSO4]: Characterization and X-ray crystal structure of 7-(2-hydroxy-4-oxo-4H-chromen-3-yl)-6H,7H-chromeno[4,3-b]chromen-6-one

被引：63

作者：

Tavakoli-Hoseini, Niloofar ^{[1
]}

Heravi, Majid M. ^{[2
]}

Bamoharram, Fatemeh F. ^{[1
]}

Davoodnia, Abolghasem ^{[1
]}

Ghassemzadeh, Mitra ^{[3
]}

机构：

[1] Islamic Azad Univ, Mashhad Branch, Dept Chem, Mashhad, Iran

[2] Alzahra Univ, Sch Sci, Dept Chem, Tehran, Iran

[3] Chem & Chem Engn Res Ctr Iran, Tehran, Iran

来源：

JOURNAL OF MOLECULAR LIQUIDS | 2011年 / 163卷 / 03期

关键词：

Biscoumarins; 4-Hydroxycoumarin; Ionic liquid; Unexpected product; ACIDIC IONIC LIQUIDS; SUPPORTED POLYPHOSPHORIC ACID; ONE-POT SYNTHESIS; REUSABLE CATALYST; SOLID ACID; EFFICIENT; DERIVATIVES; GREEN; 4-HYDROXYCOUMARIN; IMIDAZOLES;

D O I：

10.1016/j.molliq.2011.08.007

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Under solvent-free conditions and in the presence of 3-methyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate [MIM(CH2)(4)SO3H][HSO4], a Bronsted acidic ionic liquid, the reaction of aromatic aldehydes with 4-hydroxycoumarin has been investigated. A wide range of aromatic aldehydes easily undergoes condensation with 4-hydroxycoumarin to afford biscoumarins with good purity in excellent yields. However, reaction of 2-hydroxybenzaldehyde with 4-hydroxycoumarin gave, not the corresponding biscoumarin, but a tetracyclic compound, 7-(2-hydroxy-4-oxo-4H-chromen-3-yl)-6H,7H-chromeno[4,3-b]chromen-6-one, in high yield. (C) 2011 Elsevier B.V. All rights reserved.

引用

页码：122 / 127

页数：6

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