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Note | Regular issue | Vol 68, No. 4, 2006, pp.821-828
Published online, 3rd March, 2006
DOI: 10.3987/COM-06-10678
Unexpected Reaction of 2-Hydrazinoperimidine with Maleic Anhydride: Syntheses of (8-Amino-9-oxo-9,10-dihydro-8H-imidazo[1,2-a]perimidin-10-yl)acetic Acid and Its Azomethine Derivatives

Anton V. Dolzhenko, Wai-Keung Chui,* and Anna V. Dolzhenko

*Department of Pharmacy, Faculty of Science, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore

Abstract

The reaction of 2-hydrazinoperimidine (3) and maleic anhydride in mild conditions afforded the formation of an unexpected product, namely (8-amino-9-oxo-9,10-dihydro-8H-imidazo[1,2-a]perimidin-10-yl)acetic acid (5). The possible mechanism of this reaction is discussed. Schiff bases (9a-f) were prepared from 5 using corresponding aldehydes. The structures of the prepared compounds were established with spectral analysis including NOESY 2D experiments.