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An efficient hetero Diels-Alder approach to imidazo[4,5-c]pyridazines as purine analogues

✍ Scribed by Paymaneh Y.F. Deghati; Martin J. Wanner; Gerrit-Jan Koomen

Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 230 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(98)00806-5

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✦ Synopsis

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, o 1998 Elsevier Science I.Id. All rights reserved.

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