Abstract
A clean and efficient procedure is described for the synthesis of 7-(4-hydroxy-2-oxo-2H-1-benzopyran-3-yl)- 6H,7H-[1]benzopyrano[4,3-b][1]benzopyran-6-ones and 2-(2,3,4,9-tetrahydro-3,3-dimethyl-1-oxo-1H-xanthen-9-yl)-3- hydroxy-5,5-dimethyl-2-cyclohexen-1-ones from a quasi-Knoevenagel-Michael reaction sequence of salicylaldehydes with compounds having active methylene groups [4-hydroxycoumarin (4-hydroxy-2H-1-benzopyran-2-one) and dimedone (5,5-dimethyl-1,3-cyclohexanedione)] in a ratio of 1:2, in the presence of a catalytic amount of 60% Zr(HSO4)4/SiO2 as an efficient heterogeneous catalyst at 60 °C and under solvent-free conditions.
Keywords: [1] Benzopyrano[4, 3-b] [1]benzopyran-6-ones, Quasi-Knoevenagel-Michael reaction sequence, silica supported Zr(HSO4)4, solvent-free conditions, xanthenones.
Letters in Organic Chemistry
Title:Silica Supported Zr(HSO4)4 Catalyzed Solvent-free Synthesis of [1]Benzopyrano[ 4,3-b][1]benzopyran-6-ones and Xanthenones
Volume: 11 Issue: 5
Author(s): Shahrzad Abdolmohammadi
Affiliation:
Keywords: [1] Benzopyrano[4, 3-b] [1]benzopyran-6-ones, Quasi-Knoevenagel-Michael reaction sequence, silica supported Zr(HSO4)4, solvent-free conditions, xanthenones.
Abstract: A clean and efficient procedure is described for the synthesis of 7-(4-hydroxy-2-oxo-2H-1-benzopyran-3-yl)- 6H,7H-[1]benzopyrano[4,3-b][1]benzopyran-6-ones and 2-(2,3,4,9-tetrahydro-3,3-dimethyl-1-oxo-1H-xanthen-9-yl)-3- hydroxy-5,5-dimethyl-2-cyclohexen-1-ones from a quasi-Knoevenagel-Michael reaction sequence of salicylaldehydes with compounds having active methylene groups [4-hydroxycoumarin (4-hydroxy-2H-1-benzopyran-2-one) and dimedone (5,5-dimethyl-1,3-cyclohexanedione)] in a ratio of 1:2, in the presence of a catalytic amount of 60% Zr(HSO4)4/SiO2 as an efficient heterogeneous catalyst at 60 °C and under solvent-free conditions.
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Cite this article as:
Abdolmohammadi Shahrzad, Silica Supported Zr(HSO4)4 Catalyzed Solvent-free Synthesis of [1]Benzopyrano[ 4,3-b][1]benzopyran-6-ones and Xanthenones, Letters in Organic Chemistry 2014; 11 (5) . https://dx.doi.org/10.2174/1570178610666131212231709
DOI https://dx.doi.org/10.2174/1570178610666131212231709 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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