Synthesis and Antileukemic Activity of Bis[[(Carbamoyl)oxy]Methyl]-Substituted Pyrrolo[2,1-a]isoquinolines, Pyrrolo[1,2-a ]quinolines, Pyrrolo[2,1-a ]isobenzazepines, and Pyrrolo[1,2-a]benzazepines

A series of bis[[(carbamoyl)oxy] methyl]-substituted pyrrole-fused tricyclic heterocycles were synthesized by using 1,3-dipolar cycloaddition reactions with a trifluoromethanesulfonate salt of an appropriate Resissert compound or with a mesoionic oxazolone intermediate. All of the bis(carbamates) were active in vivo against P388 lymphocytic leukemia with 5,6-dihydro-8-methoxy-1,2-bis(hydroxymethyl)pyrrolo[2,1-a]isoquinoline bis [N-(2-propyl)carbamate] (3c) showing the highest level of activity.