Tetrahedron Letters p. 4561 - 4564 (1998)
Update date:2022-08-02
Topics:
Deghati, Paymaneh Y.F.
Wanner, Martin J.
Koomen, Gerrit-Jan
A general approach to 3-deaza-6-azapurine by a hetero Diels-Alder reaction is described. Reaction of sulfonamide protected 5-vinylimidazole with 4-phenyl-1,2,4-triazoline-3,5-dione in methanol gave the Diels-Alder adduct 8 in 85% yield. Deprotection of the resulting N-phenyltriazole was efficiently accomplished by ring opening with hydrazine followed by heating in DMSO. The completely deprotected and aromatized purine analogue 1 was obtained directly from this one-pot reaction in 48% yield.
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