A series of 2-amino-3-ethoxycarbonyl-4-aryl-4H,5H-pyrano-[3,2-c]benzopyran-5-ones have been were synthesised by the reaction of 4-hydroxycoumarin, an aromatic aldehyde and ethyl cyanoacetate under microwave irradiation with short times and high yields.
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X-ray crystallography for 4c: Empirical formula C21H16NO5, FW=397.80, T=296(2)K, triclinic, space group P-1, a=5.756(1)Å, b=10.099(1)Å, c=17.106(2)Å, α=80.49(1)°, β=83.13 (1)°, γ=80.07(1)° V=961.8 (3)Å3, Z=2, Dc=1.374 Mg/m3, λ(MoKα)=0.71073Å, μ= 0.231 mm−1, F(000)=412, 1.21°<θ<25.25°, R=0.0369, wR=0.0947. S=1.029, Largest diff. Peak and hole: 0.213 and −0.264e. ≈−3. The ethyl group of the ester side chain is disordered. Hydrogen bonding occurs between the NH2 group and the carbonyl of the ethoxycarbonyl at reasonable distances, Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. CCDC 226407. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax(+44) 1223-3366-033; e-mail: deposit@ccdc.cam.ac.uk).
