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Issue 39, 2014
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Ultrasound-assisted 1,3-dipolar cycloaddition and cyclopropanation reactions for the synthesis of bis-indolizine and bis-cyclopropane derivatives

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Abstract

Ultrasound irradiation can promote the 1,3-dipolar cycloaddition reaction of 2-chloropyridinium ylides with 2-benzylidenemalononitrile or 2,2′-(1,4-phenylenebis(methanylylidene))dimalononitrile, to afford the indolizine and bis-indolizine derivatives respectively. While the reaction of pyridinium ylides with 2-benzylidenemalononitrile or 2,2′-(1,4-phenylenebis(methanylylidene))dimalononitrile under ultrasound irradiation provided, in an unusual manner, cyclopropane and bis-cyclopropane derivatives, respectively. These cycloaddition and cyclopropanation reactions were carried out in the presence of triethylamine, in acetonitrile, at room temperature.

Graphical abstract: Ultrasound-assisted 1,3-dipolar cycloaddition and cyclopropanation reactions for the synthesis of bis-indolizine and bis-cyclopropane derivatives

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Article information


Submitted
24 Jun 2014
Accepted
07 Aug 2014
First published
07 Aug 2014

Org. Biomol. Chem., 2014,12, 7859-7863
Article type
Paper

Ultrasound-assisted 1,3-dipolar cycloaddition and cyclopropanation reactions for the synthesis of bis-indolizine and bis-cyclopropane derivatives

M. Abaszadeh and M. Seifi, Org. Biomol. Chem., 2014, 12, 7859
DOI: 10.1039/C4OB01305K

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