Highly diastereoselective synthesis of C6-functionalized dihydroimidazotriazines.
[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.
Garnier
Ethel
E
Institut de Chimie Organique et Analytique (ICOA), UMR-CNRS 6005, Laboratoire de Recherche Correspondant CEA numéro M09, Université d'Orléans, France.
Guillard
Jérôme
J
Pasquinet
Eric
E
Suzenet
Franck
F
Poullain
Didier
D
Jarry
Christian
C
Léger
Jean-Michel
JM
Lebret
Bruno
B
Guillaumet
Gérald
G