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Paper | Regular issue | Vol 55, No. 4, 2001, pp.671-688
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9145
Novel Approaches to Optically Active Substituted 4,5-Dihydro-1,2,4-triazin-6(1H)-ones as Conformationally Constrained Peptidomimetics

Laurènt Saniere, Martine Schmitt, Nadia Pellegrini, and Jean-Jacques Bourguignon*

*Laboratoire de Pharmacochimie de la Communication Cellulaire, UMR 7081 du CNRS, Faculté de Pharmacie,74 route du Rhin, 67400 Illkirch, France


Synthesis of 4,5-dihydro-1,2,4-triazin-6-ones bearing different chiral a-amino acid residues at the C3 and N1 positions are reported. Cyclocondensation of N-hioacylphthalimides with α-amino hydrazides afforded C3 functionalised dihydrotriazinones in good yields without detectable epimerisation. Moreover, N1-alkylation of the dihydrotriazinone ring with several α-bromo esters was performed with satisfactory yields. Interestingly, this alkylation reaction was found to be regioselective with respect to N4 and NHBoc. This class of compounds represents a new series of small conformationally constrained peptide derivatives.