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

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.A. V. Bogatskii Physicochemical Institute, National Academy of Sciences of Ukraine, Odessa 270080. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 824–827, June, 1988.