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1053245 
Journal Article 
Synthesis of 3-hydroxy-6-oxo[1,2,4]triazin-1-yl alaninamides, a new class of cyclic dipeptidyl ureas 
Sañudo, M; Marcaccini, S; Basurto, S; Torroba, T 
2006 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
71 
12 
4578-4584 
English 
16749791 
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.