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1343939 
Journal Article 
SIMULTANEOUS CONVERSION OF N-(1)-(2-AMINOETHYL)ADENOSINE TO N-6-(2-AMINOETHYL)-ADENOSINE AND TRICYCLIC 1,N-6-ETHANOADENOSINE UNDER MILD AQUEOUS CONDITIONS 
Buckmann, AF; Wray, V; Vanderplas, HC 
1995 
Yes 
Heterocycles
ISSN: 0385-5414 
41 
7 
1399-1419 
WOS:A1995RH11500004 
Under mild aqueous conditions (50 degrees C, pH range 6 - 7)
N(1)-(2AE)-adenosine (2) can be converted to N-6-(2AE)-adenosine (7) by Dimroth rearrangement at
unexpectedly high rate. In a parallel reaction tricyclic 1,N-6-ethanoadenosine (6) is formed. The
latter reaction is new in heterocyclic organic chemistry and is strongly catalysed by the
monoanions of phosphoric and arsenic acid and, less strongly, by the acetate anion.