1-Azatriptycenes via palladium catalyzed reactions

ORGN 549

Elleanor Rio C. Andaya, andayae@unr.nevada.edu and Thomas W. Bell. Department of Chemistry, University of Nevada Reno, 1664 North Virginia St., Reno, NV 89557-0216
1-Azatriptycene is a compound with a di-π-methane system, similar to triptycene, except that one of the bridgehead methane positions contains nitrogen instead of carbon. Synthesis of 1-azatriptycene was first published in 1964 via the internal nucleophilic addition to a benzyne. Our study involves synthesis of an azatriptycene through palladium catalyzed amination of arenes (the Buchwald-Hartwig reaction). In the synthetic route under current investigation, the desired azatriptycene has a methyl substituent in the 6-position to avoid unwanted side reactions. This poster presents our progress towards the synthesis of 1-azatriptycenes.