Fused Polycyclic Nitrogen-Containing Heterocycles: VI.* Pyrrolo[1,2-a]quinoxalines


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Abstract

3-(β-Chlorobenzyl)-1,2-dihydroquinoxalin-2-one reacts with anions derived from acetylacetone, benzoylacetone, dibenzoylmethane, malononitrile, ethyl acetoacetate, and ethyl cyanoacetate to give the corresponding 3-(β-R,R'CH-benzyl)-1,2-dihydroquinoxalin-2-ones which undergo intramolecular cyclocondensation to functionally substituted pyrrolo[1,2-a]quinoxalines on heating in boiling acetic acid. The reaction of 3-(α-chloro-p-nitrobenzyl)-1,2-dihydroquinoxalin-2-one with acetylacetone anion directly leads to the corresponding pyrrolo[1,2-a]quinoxaline, without heating in acetic acid.

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