AN EFFICIENT HETERO-DIELS-ALDER APPROACH TO IMIDAZO[4,5-C]PYRIDAZINESAS PURINE ANALOGS

Authors
DEGHATI PYF WANNER MJ KOOMEN GJ
Citation
Pyf. Deghati et al., AN EFFICIENT HETERO-DIELS-ALDER APPROACH TO IMIDAZO[4,5-C]PYRIDAZINESAS PURINE ANALOGS, Tetrahedron letters, 39(25), 1998, pp. 4561-4564
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
25
Year of publication
1998
Pages
4561 - 4564
Database
ISI
SICI code
0040-4039(1998)39:25<4561:AEHATI>2.0.ZU;2-B
Abstract
A general approach to 3-deaza-6-azapurine by a hetero Diels-Alder reac tion is described. Reaction of sulfonamide protected 5-vinylimidazole with 4-phenyl-1,2,4-triazoline-3,5-dione in methanol gave the Diels-Al der adduct 8 in 85% yield. Deprotection of the resulting N-phenyltriaz ole was efficiently accomplished by ring opening with hydrazine follow ed by heating in DMSO. The completely deprotected and aromatized purin e analogue 1 was obtained directly from this one-pot reaction in 48% y ield. (C) 1998 Elsevier Science Ltd. All rights reserved.