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Synthesis 1988; 1988(2): 154-155
DOI: 10.1055/s-1988-27500
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4-Nitrobenzyl as a N-Protective Group in N-Heterocycles: An Easy Access to 7-Arylmethyladenines from 3-(4-Nitrobenzyl)-adenine

Abderahman Er-Rhaimini* , René Mornet
  • *Groupe de Recherches de Chimie Organique et Bioorganique, Université d'Angers, 2 Boulevard Lavoisier, F-49045 Angers CEDEX, France
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Publikationsdatum:
20. August 2002 (online)

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The 4-nitrobenzyl group is used as a N-3 protective group in adenine to direct further alkylation (benzylation) at the 7-position. In the obtained 7-arylmethyl-3-(4-nitrobenzyl)adenines, this protective group is removed, presumably as quinonimine methide, by reduction of the nitro group by the use of sodium dithionite, thus leaving 7-arylmethyladenines.