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Synthesis 2010(14): 2424-2436  
DOI: 10.1055/s-0029-1218796
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Synthesis of New 4-Arylideneimidazolin-5-ones Related to the GFP Chromophore by 2+3 Cyclocondensation of Arylideneimines with Imidate Ylides

Anthony Baldridge, Janusz Kowalik*, Laren M. Tolbert
School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332-0400, USA
Fax: +1(404)8947452; e-Mail: janusz.kowalik@chemistry.gatech.edu;
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Publication History

Received 22 December 2009
Publication Date:
20 May 2010 (online)

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Abstract

A 2+3 condensation of a wide assortment of Schiff bases, prepared from aromatic aldehydes and primary amines, with methyl 2-(1-ethoxyethylideneamino)acetate allows convenient access to an extensive family of substituted 4-arylideneimidazolin-5-one analogues of the green fluorescent protein (GFP) chromophore.

Key words

4-arylideneimidazolin-5-one - azomethine ylide - Schiff bases - heterocycle - 2+3 cycloaddition

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