Chemistry of Halonitroethenes, 1: First Synthesis of Functionalized 3-Chloroquinoxalin-2(1H)-one 4-Oxides

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...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2008-08, Vol.2008 (16), p.2575-2581
Main Authors: Meyer, Christian, Zapol’skii, Viktor A., Adam, Arnold E., Kaufmann, Dieter E.
Format: Article
Language:English
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Summary: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 S N Vin 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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2008-1067207