Synthesis of mono-NH cross-bridged tetraazamacrocycles

ORGN 292

Matthew J. Young1, Gary R. Weisman, gary.weisman@unh.edu1, Edward H. Wong, ehw@cisunix.unh.edu1, and Carolyn J. Anderson, andersoncj@wustl.edu2. (1) Department of Chemistry, University of New Hampshire, Durham, NH 03824, (2) Division of Radiological Sciences, Washington University School of Medicine, St. Louis, MO 63110
The cross-bridged cyclen- and cyclam-based tetraazamacrocycles are able to form more kinetically inert metal complexes than their non-bridged counterparts. An allyl protecting group has been utilized that allows for greater synthetic versatility when preparing mixed pendant armed variations on the cross-bridged cyclam and cyclen motifs. This orthogonal deprotection occurs via an efficient microwave assisted synthesis using tBuOK in DMSO for 45 minutes at 100 °C to remove the allyl group selectively over the benzylic sites on the macrocycle.

 

Heterocycles and Aromatics
8:00 AM-11:40 AM, Tuesday, April 8, 2008 Morial Convention Center -- Rm. R06, Oral

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008