Abstract
An unexpected intramolecular cyclization during the reaction of furfurylamine with maleimides is reported as a novel strategy for the efficient green synthesis of the 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton. Under the same reaction conditions, 7-oxabicyclo[2.2.1]hept-5-enes were synthesized when furfurylamine was N-protected by the acetyl group. Both types of bicycloheptenes were screened using the zebrafish model system for genetics and developmental biology.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis
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Bridged Bicyclo Compounds, Heterocyclic / chemistry
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Bridged Bicyclo Compounds, Heterocyclic / pharmacology*
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Bridged Bicyclo Compounds, Heterocyclic / toxicity
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Cyclization
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Dose-Response Relationship, Drug
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Embryonic Development / drug effects*
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Furans / chemistry*
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Inhibitory Concentration 50
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Maleimides / chemistry*
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Models, Animal*
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Molecular Structure
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Phenotype
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Structure-Activity Relationship
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Zebrafish / embryology*
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Zebrafish / genetics
Substances
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7-oxa-2-azabicyclo(2.2.1)hept-5-ene
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Bridged Bicyclo Compounds, Heterocyclic
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Furans
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Maleimides
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furfurylamine