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Paper | Regular issue | Vol 75, No. 11, 2008, pp.2761-2767
Published online, 16th June, 2008
DOI: 10.3987/COM-08-11447
Mannich Reaction of 5-Hydroxy-β-carboline. Application to the Synthesis of Novel Oxazinopyrimidocarboline Derivatives

Samar Issa, Nadia Walchshofer, Issam Kassab, Jacques Gentili, Aziz Geahchan, and Zouhair Bouaziz*

*University of Lyon, Lyon, F-69003, France

Abstract

5-Hydroxy-β-carboline 4 was synthesized and submitted to the Mannich reaction towards formaldehyde and some primary amines. It undergoes an original reaction of bis-aminomethylation-cyclisation giving the oxazinopyrimidocarboline derivatives 5a-d. The structure of these compounds was confirmed by their high-resolution mass, IR, 1H NMR and 13C NMR spectral data.