Synthesis of 3-hydroxy-6-oxo[1,2,4]triazin-1-yl alaninamides, a new class of cyclic dipeptidyl ureas.
Cyclohexyl or benzyl isocyanide, benzoyl-, or 4-methoxybenzoylformic acid and semicarbazones underwent Ugi reactions in methanol for 3 days to give the Ugi adducts, which were then stirred with sodium ethoxide in ethanol for 12 h to give 3-hydroxy-6-oxo[1,2,4]triazin-1-yl alaninamides. The X-ray diffraction structure of the first example showed the tautomer having the proton in the O2 atom that was fixed in the crystal by packing in dimers with a H-bond distance of 1.9 A. Selected [1,2,4]triazines were treated with diazomethane for 12 h to get the O-methyl derivatives. Both hydroxy and O-methyl derivatives obtained by this method constitute a new class of pseudopeptidic [1,2,4]triazines composed of two different amino acids, arylglycine and alanine derivatives, in which the N-terminal arylglycine and the peptidic amide nitrogen atoms are bonded through a urea moiety.
Sañudo
María
M
Química Orgánica, Facultad de Ciencias, Universidad de Burgos, 09001 Burgos, Spain.
Marcaccini
Stefano
S
Basurto
Sara
S
Torroba
Tomás
T
D000577:Amides / Q000138:chemical synthesis; D019281:Dimerization; D004151:Dipeptides; D006860:Hydrogen Bonding; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D014508:Urea / Q000138:chemical synthesis*; D014961:X-Ray Diffraction
D000577:Amides; D004151:Dipeptides; D010456:Peptides, Cyclic; D014508:Urea