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DOI: 10.1055/s-2007-990775
One-Pot Three-Component Synthesis of 3-Amino-5,8-dioxo-5,8-dihydro-1H-pyrazolo[1,2-a]pyridazines
Publikationsverlauf
Publikationsdatum:
11. September 2007 (online)
Abstract
The reactive 1:1 zwitterionic intermediate formed by the addition of isocyanides to dialkyl acetylenedicarboxylates was trapped by 3,6-dihydroxypyridazine to produce 3-amino-5,8-dioxo-5,8-dihydro-1H-pyrazolo[1,2-a]pyridazines in good yields.
Key words
multicomponent reactions - pyrazolo[1,2-a]pyridazines - isocyanides - cyclizations - heterocycles
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References
Selected X-ray crystallographic data for compound 8d: C15H19N3O6, M r 337.33; crystal size: 0.4 × 0.3 × 0.2 mm; crystal system: triclinic; a = 8.882 (3), b = 10.0398 (13), c = 10.730 (3) Å, α = 71.481 (18), β = 67.10 (3), γ = 81.148 (17)°; space group P-1; Z = 2, V = 835.3 (4) Å3, D calc. = 1.341 g cm-3; R = 0.0446, R w = 0.1258; -11 ≤ h ≤ 6; -12 ≤ k ≤ 12; -13 ≤ l ≤ 12; MoK α radiation (λ = 0.71073 Å); T = 290 (2) K. CCDC 630958 contains the supplementary crystallographic data of compound 8d. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via the internet (http://www.ccdc.cam.ac.uk/data_request/cif), e-mail (data_request@ccdc.cam.ac.uk), or fax (+44 1223 336033).