Novel synthesis and reactions of 1,4,7-trimethyl-4,5,7,8-tetrahydro-6h-imidazo[4,5-e][1,4]diazepine-5,8-dione - A cyclic caffeine analog

Article abstract of DOI:10.1007/BF02252283

The synthesis of a cyclic homolog of caffeine is reported. Its 2-nitro- and 2-amino derivatives were obtained for the first time. It was shown that the 2-bromo and 2-chloro substituted cyclic homologs react with nucleophiles under basically identical conditions. Whereas 8-bromocaffeine can give a normal Ullman reaction product via heating with powdered copper in ethylene glycol, the homolog gives only a reduction product and does not react with potassium thiocyanate or cyanide. 1998 Plenum Publishing Corporation.