ORGN 520 |
| Regiospecificity for N9 alkylation of purines in excellent yields with various alkyl iodides was achieved with the assistance of 6-heteroaryl substituents. Effective protection of N7 by such 6-heteroaryl groups was observed, and this was rationalized by the coplanar conformations indicated by theoretical calculations (MM2, RHF/6-31 G*, B3LYP/6-31+ G*) and X-ray crystal structures. Alkylation of 2-chloro/amino-6-heteroarylpurines also gave N9-alkylpurines exclusively, and a coplanar conformation was shown to be required for such regioselective N9 alkylations.
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New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
