P. Langer et al., REGIOSELECTIVE CYCLIZATIONS OF DELOCALIZED 1,3-AMIDE DIANIONS WITH OXALIC-ACID DIELECTROPHILES, Liebigs Annalen, (12), 1997, pp. 2553-2561
A novel strategy for the synthesis of nitrogen-rich heterocycles by re
gioselective C,N-cyclization of ambident dianions with oxalimidoyl dic
hlorides is reported. One-pot reactions provide gamma-iminotetramic ac
id amides 1, radialenes 2 and tetraimino-diazaspiro[4.4]nonenones 3. C
hemical properties and structural features of the new heterocyclic sys
tems, including the tautomerism of 2, were investigated.