ORGN 373 |
| Maghar S. Manhas1, Ajay K. Bose1, Subhendu N. Ganguly1, Atri Guha1, and Reddy Damavarapu2. (1) Department of Chemistry and Chemical Biology, Stevens Insitute of Technology, Castle Point on Hudson, Hoboken, NJ 07030, (2) Picatinny Arsenal, Dover NJ, Dover, NJ 07806 |
| Some amines and aldehydes can condense under acid conditions to form heterocycles of unusual structures. Thus, the reaction between p- toluidine (1), formaldehyde and HCl after 8h of reflux produces Troger's base (2) that is formed by the assembly of two molecules of (1) linked by three methylene groups derived from formaldehyde. Similar reaction between benzylamine (3) and glyoxal (4) at room temperature for several hours leads to a cage compound, hexabenzyl-hexaaza-isowurtzitane (5), by linking six molecules of (3) with three molecules of (4) . Compound (5) is an intermediate of the explosive CL - 20. We have observed that when the conventional reactions are conducted under microwave irradiation for a few minutes, the target compounds (2) and (5) are obtained in good yield and high purity. Interestingly, Troger's base can also be prepared in good yields in less than thirty min by "Grindstone Chemistry", i.e., by grinding a mixture of the solid and liquid reactants in a mortar and pestle. The extension of these preparative methods for the synthesis of analogs will be discussed. |
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Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster
Division of Organic Chemistry |