title: Highly diastereoselective synthesis of C6-functionalized dihydroimidazotriazines.
abstract: [reaction: see text] 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 1a-c 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 (1)H and (13)C NMR spectra analysis. The process was shown to be totally regio- and diastereoselective. A mechanism involving an imine intermediate was proposed.
authors: Institut de Chimie Organique et Analytique (ICOA), UMR-CNRS 6005, Laboratoire de Recherche Correspondant CEA numéro M09, Université d'Orléans, France.
authors: Ethel
authors: E
authors: Garnier
authors: Jérôme
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authors: Guillard
authors: Eric
authors: E
authors: Pasquinet
authors: Franck
authors: F
authors: Suzenet
authors: Didier
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authors: Poullain
authors: Christian
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authors: Jarry
authors: Jean-Michel
authors: JM
authors: Léger
authors: Bruno
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authors: Lebret
authors: Gérald
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authors: Guillaumet