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?

Organic & Biomolecular Chemistry Pub Date: 2012-10-22 DOI: 10.1039/C2OB26699G

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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