Issue 3, 2013
From the journal:

Organic & Biomolecular Chemistry

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†

Carlos E. Puerto Galvisa  and  Vladimir V. Kouznetsov*a  

* Corresponding authors

a Laboratorio de Química Orgánica y Biomolecular, Universidad Industrial de Santander, Cra 27 calle 9, Bucaramanga A.A. 678, Colombia
E-mail: kouznet@uis.edu.co
Fax: +57 76 349069

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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Article information

DOI
https://doi.org/10.1039/C2OB26699G
Article type
Communication
Submitted
29 Aug 2012
Accepted
19 Oct 2012
First published
22 Oct 2012

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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