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Issue 3, 2013
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An unexpected formation of the novel 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton during the reaction of furfurylamine with maleimides and their bioprospection using a zebrafish embryo model

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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.

Graphical abstract: An unexpected formation of the novel 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton during the reaction of furfurylamine with maleimides and their bioprospection using a zebrafish embryo model

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Publication details

The article was received on 29 Aug 2012, accepted on 19 Oct 2012 and first published on 22 Oct 2012


Article type: Communication
DOI: 10.1039/C2OB26699G
Citation: Org. Biomol. Chem., 2013,11, 407-411
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    An unexpected formation of the novel 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton during the reaction of furfurylamine with maleimides and their bioprospection using a zebrafish embryo model

    C. E. Puerto Galvis and V. V. Kouznetsov, Org. Biomol. Chem., 2013, 11, 407
    DOI: 10.1039/C2OB26699G

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