Diazabicycloalkanes with nitrogen atoms in bridgehead positions. 16. Synthesis and properties of benzo[b]-1,4-diazabicyclo[2.2.2]octene and dibenzo[b,e]-1,4-diazabicyclo[2.2.2]octadiene, containing primary aromatic amino acids

Abstract

4′-Aminobenzo[1′,2′-b]-1,4-diazabicyclo[2.2.2]octene and 4′-aminodibenzo[1′,2′-b, e]-1,4-diazabicyclo[2.2.2]octadiene have been prepared by cyclization reactions of N-Β-chloroethyl derivatives of 1,2,4-triaminobenzene and aminophenazine, and subsequent catalytic hydrogenation of the corresponding 4′-nitrobenzo[1′,2′-b]-1,4-diazabicyclo[2.2.2]octene and 4-benzylaminodibenzo[1′,2′-b,e]-1,4-diazabicyclo[2.2.2]-octadiene. Using the conversion of these compounds to azides as an example, we have demonstrated the feasibility of applying these primary aromatic amines for the synthesis of derivatives of these heterocycles.