ORGN 177 |
| 2-Amino-2-imidazolidines are found in many important biologically and pharmaceutically active compounds. This poster describes the development of a new methodology for the synthesis of the 2-amino-2-imidazolines as depicted below. Treatment of amino azide 1 with triphenylphosphine and an isocyanate yields 2-amino-2-imidazoline 4 in moderate to good yields. Optimization studies indicate that higher yields are achieved when R 2 = Ts. Furthermore, we have also determined that the N-Ts group can be cleaved from 4 using samarium diiodide. We speculate that that the formation of 4 involves an aza-Wittig reaction of iminophosphorane 2 with the isocyanate to yield carbodiimide 3 , which undergoes further ring closure. Application of this new methodology to the synthesis of analogues of NA22598A 1 will also be disclosed.
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Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster
Sci-Mix
Division of Organic Chemistry |
