One-Pot Three-Component Synthesis of 3-Amino-5,8-dioxo-5,8-dihydro-1H-pyrazolo[1,2-a]pyridazines

Mehdi Adib; Somayeh Aali Koloogani; Alireza Abbasi; Hamid Reza Bijanzadeh

doi:10.1055/s-2007-990775

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Synthesis 2007(19): 3056-3060
DOI: 10.1055/s-2007-990775

PAPER

One-Pot Three-Component Synthesis of 3-Amino-5,8-dioxo-5,8-dihydro-1H-pyrazolo[1,2-a]pyridazines

Mehdi Adib*^a, Somayeh Aali Koloogani^a, Alireza Abbasi^a, Hamid Reza Bijanzadeh^b
^a School of Chemistry, University College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran
Fax: +98(21)66495291; e-Mail: madib@khayam.ut.ac.ir;
^b Department of Chemistry, Tarbiat Modarres University, PO Box 14115-175, Tehran, Iran

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Publication History

Received 20 April 2007
Publication Date:
11 September 2007 (online)

Abstract
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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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18

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).