Regioselective synthesis of 7,8-dihydroimidazo[5,1-c][1,2,4]triazine-3,6(2H,4H)-dione derivatives: A new drug-like heterocyclic scaffold

• Nikolay T. Tzvetkov,
• Harald Euler and
• Christa E. Müller

Beilstein J. Org. Chem. 2012, 8, 1584–1593, doi:10.3762/bjoc.8.181

• introduced. The synthetic strategy allows broad structural variation of this new drug-like heterobicyclic scaffold. In addition to extensive NMR and MS analyses, the structure of one derivative was confirmed by X-ray crystallography. Keywords: hydantoins; hydrazides; imidazotriazines; N-alkylation; regio

• - and chemoselective reaction; thionation; X-ray structure; Introduction Imidazotriazines represent an important class of condensed heterobicycles that display a variety of significant biological activities, including anticancer [1], antimicrobial [2], anti-inflammatory [3] and neuroprotective [4

• multigram scale. Finally, the imidazotriazines were further functionalized by an N-alkylation reaction using different alkylating reagents under basic conditions (Scheme 3). Alkylation of 24 with methyl iodide led to 26, whereas methyl methanesufonate was used as an alkylating reagent for the methylation of