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

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 pyridini...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2014-10, Vol.12 (39), p.7859-7863
Main Authors: Abaszadeh, Mehdi, Seifi, Mohammad
Format: Article
Language:English
Subjects:
Cycloaddition Reaction
Cyclopropanes - chemical synthesis
Cyclopropanes - chemistry
Indolizines - chemical synthesis
Indolizines - chemistry
Pyridines - chemistry
Ultrasonics
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob01305k