Polycyclic N-Hetero Compounds. X. Reactions of 1, 3-Cyclohexanedione and Its Dimer with Formamide or Trisformylaminomethane

Abstract

Condensation of 1, 3-cyclohexanedione (I) with formamide gave 9, 10-dihydro-1, 3, 5, 7-tetraazaphenanthrene (II), 1, 2, 3, 4, 5, 6, 7, 8, 9, 10-decahydro-11, 13-diazabenzo [g] chrysene-1, -5-dione (III), 1, 2, 5, 6-tetrahydro-3, 7, 9, 11, 13-pentaazadibenzophenanthrene (IV), and 7, 8, 13, 14-tetrahydro-2, 4, 6, 10, 12-pentaazabenzo [c] chrysene (V). Dehydrogenation of II with sulfur gave 1, 3, 5, 7-tetraazaphenanthrene (VI). To make sure the formation mechanism of IV and V, dimer of I (enol form of VII') was heated with formamide or trisformyl-aminomethane and the formation of IV and V were confirmed.