Abstract
A new synthesis of unsymmetrically substituted imidazo[1,2-a]quinoxalines via regioselective displacement of 3-chloro group in 2-(methylthio)-3-chloroquinoxalines by aminoacetaldehyde dimethylacetal and subsequent-acid mediated intramolecular cyclization of the resulting adducts is reported in this study. The utility of the 3-(methylthio) group in these imidazoquinoxalines is also demonstrated by conversion of one of the 2-(methylthio)quinoxalines to 2-(methylsulfonyl) derivative and its subsequent displacement by hydroxy-, phenoxy- and n-butylamino groups, thus affording various 2-substituted imidazo[1,2-a]quinoxalines.
Keywords: Imidazo[1, 2-a]quinoxalines, aminoacetaldehyde dimethylacetal, chloroquinoxalines, (methylsulfonyl)imidazo[1, 2- a]quinoxalines, anti-allergic, unsymmetrically.
Graphical Abstract
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