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Highly Diastereoselective Synthesis of C(6)-Functionalized Dihydroimidazotriazines

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journal contribution
posted on 27.11.2003, 00:00 by Ethel Garnier, Jérôme Guillard, Eric Pasquinet, Franck Suzenet, Didier Poullain, Christian Jarry, Jean-Michel Léger, Bruno Lebret, Gérald Guillaumet
The first examples of C(6)-substituted 7-hydroxy-6,7-dihydro-5H-imidazo[1,2-b][1,2,4]triazines have been prepared by ring closure of different 5(2H)-1,2,4-triazin-3-ones 1ac with 40% aqueous glyoxal and various nucleophiles (alcohols, thiols, or amines). The structure and exact stereochemistry of 2a was established by a single X-ray diffraction study and 1H and 13C NMR spectra analysis. The process was shown to be totally regio- and diastereoselective. A mechanism involving an imine intermediate was proposed.