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DOI: 10.1055/s-2008-1067207
Chemistry of Halonitroethenes, 1: First Synthesis of Functionalized 3-Chloroquinoxalin-2(1H)-one 4-Oxides
Publication History
Publication Date:
30 July 2008 (online)
Abstract
A one-pot annulation reaction of aniline and its ring-substituted derivatives with 1,1,2-trichloro-2-nitroethene (TCNiE) was developed delivering 3-chloroquinoxalin-2(1H)-one 4-oxides, exclusively, in good yields. The structure was proved by X-ray analysis. The C-N cyclization, a competing reaction to the double SNVin reaction of 1,1,2-trichloro-2-nitroethene with amines, can be controlled by the mode of addition. Some of the resulting quinoxalinones are promising candidates with respect to their prospective biological, especially pharmacological, activity.
Key words
annulation - C-N coupling - amines - halides - nitro compounds - nitrones - quinoxalinones
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References
X-ray crystallographic analysis of C21H32N2O3S was performed at 223(2) K by using a STOE IPDS II diffractometer with MoKα radiation (λ = 0.71073 Å) and a graphite monochromator. Crystal system: triclinic, P1 (No. 2), Z = 1, a = 632.32(13) pm, b = 900.7(2) pm, c = 1935.2(4) pm, α = 84.236(19), β = 83.827(17), γ = 77.126(18), VEZ = 1064.9(4) 106 pm³. The structure was solved by direct methods (SHELXS-97)¹0a using 3704 independent reflections. Structure refinement: full matrix least-squares methods on F² using SHELXL-97¹0b all nonhydrogen atoms with anisotropic displacement parameters. All hydrogen atoms were taken from a difference Fourier synthesis and were isotropically refined. The refinement converged to a final wR2 = 0.1223 for 3704 unique reflections and R1 = 0.0540 for 2420 observed reflections [I 0 > 2σ(I 0)] and 373 refined parameters with a goodness-of-fit of 1.053. Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-679570. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033, e-mail: deposit@ccdc.cam.ac.uk].