Electrophilic Amination of Adenines. Formation and Characteristics ofN-Aminoadenines
- 1 January 1996
- journal article
- research article
- Published by Taylor & Francis in Nucleosides and Nucleotides
- Vol. 15 (1-3) , 219-233
- https://doi.org/10.1080/07328319608002381
Abstract
Amination of adenine with H2N-O-SO3H in alkaline media afforded 1-, 3-, 7-and 9-aminoadenine isomers at a ratio of about 1:1:3:1. In neutral media, the product ratio of the isomers changed to about 3:1:1:0. These results were different from the regioselectivity obtained by methylation of adenine with dimethyl sulfate under similar conditions. Amination of adenine with dinitrophenoxyamine in DMF gave 1-aminoadenine as the main product and this regioselectivity was also different from that of methylation with cH3I. Chemical characteristics of these N-amino adenines are described.Keywords
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