ORGN 58 |
| Heterocycles are among the most important classes of chemical substances which are particularly well represented among numerous natural products, pharmaceuticals and agrochemicals. Effective methodology for the synthesis of low molecular weight, functional heterocycles bearing appropriate pharmacophoric features is being continually developed for the drug discovery arena. Therefore, procedures for the efficient synthesis of low molecular weight heterocyclic systems (both aromatic and saturated analogs) that possess sites for further functionalization are attracting great interest in part, to the large growing number of valuable pharmaceutical agents that possess heterocyclic structural subunits. Over recent years, we have reported numerous efficient methods for the construction of carbon-heteroatom bonds using cesium bases. As a direct application of our methodology, we present herein, a convenient, “one-pot”, synthesis of numerous oxygen, nitrogen, sulfur, and phosphorus heterocycles. In the presence of cesium hydroxide, molecular sieves and anhydrous DMF at room temperature, various 1,2-diols, diamines, dithiols and diphosphines underwent ring closures with a plethora of dihalides to afford a wide array of structurally diverse heterocycles of varying ring size. In addition, heterocycles containing mixed donor atoms (e.g. aminoalcohols, mercaptoalcohols, aminophenols, thiophenols, etc.) were also efficiently prepared and will be reported.
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Heterocycles and Aromatics
1:00 PM-5:20 PM, Sunday, 26 March 2006 Georgia World Congress Center -- C301, Oral
Division of Organic Chemistry |
