ORGN 50 |
| The synthesis of a 152 member discovery library of 3-pyrroline containing amides was achieved by a 4-step reaction sequence. Diversification was introduced at three different sites: the substituents on the 3-pyrroline unit (R2, R3, R4), on the nitrogen atom (R1) and the amide (R). The 3-pyrroline scaffold was synthesized in excellent yields by a silver-catalyzed intramolecular cyclization of aminoallenes. N-alkyl and N-acyl diversifications (R1) were introduced by reductive amination and acylation reactions. Maximum diversity was introduced in the final step of the reaction sequence by taking advantage of the carboxylic acid handle of the 3-pyrroline subunit. Amide coupling reactions using polystyrene (PS)-carbodiimide under microwave irradiation gave very good yields of 3-pyrroline amides in greater than 85 % purity by LC/MS. This library is currently being evaluated for biological activity.
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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 |
