Electrophilic amination of adenines. Formation and characteristics of N-aminoadenines

Article abstract of DOI:10.1080/07328319608002381

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.

Full text of DOI:10.1080/07328319608002381

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Nucleosides and Nucleotides
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Electrophilic Amination of Adenines.
Formation and Characteristics of N-
Aminoadenines
Tetsuya Saga a , Toyo Kaiya a , Shoji Asano a & Kohfuku Kohda a
a Faculty of Pharmaceuticul Sciences, Nagoya City University
Tanabedori , Mizuho-ku, Nagoya, 467, Japan
Published online: 21 Aug 2006.
To cite this article: Tetsuya Saga , Toyo Kaiya , Shoji Asano & Kohfuku Kohda (1996) Electrophilic
Amination of Adenines. Formation and Characteristics of N-Aminoadenines, Nucleosides and
Nucleotides, 15:1-3, 219-233
To link to this article: http://dx.doi.org/10.1080/07328319608002381
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