N→N Alkyl and Glycosyl Migrations of Purines and Pyrimidines. I. A New Migration of 3-Alkyl-N<SUP>6</SUP>-acyladenine

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Benzyl, allyl and 3-methyl-2-butenyl groups were found to migrate from N-3 to N-9 or N-7 position of the N6-acyladenines. On heating in the presence of hydrogen halide, 3-benzyl-N6-acyladenines underwent intermolecular benzyl migration giving rise to 9-benzyl derivatives and a small amounts of the 7-benzyl isomers. 3-Methyl-2-butenyl group in N6-acyltriacanthine migrated under similar conditions to afford the 9-(3-methyl-2-butenyl) derivatives, whereas mercuric halide or cyanide caused intramolecular rearrangement to give the 9-(1, 1-dimethyl-2-propenyl) isomers.

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