Facile Synthesis and Nitration of cis-syn-cis-2,6-Dioxodecahydro-1H,5H-diimidazopyrazine

Article abstract of DOI:10.1021/jo00010a043

The title ring system was synthesized for the first time by acid-promoted condensation of ureas with 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine.Nitrosation and nitration of the polycycle occurs first at the piperazine nitrogens.Successive further nitration leads to tetra-, penta-, and hexanitro derivatives.X-ray crystallographic analysis of the tetra- and hexanitro derivatives established the cis-syn-cis configuration and an all-axial conformation for this ring system.Possible reasons for the stereoselectivity of the condensation reaction are discussed.