An efficient synthesis of 1,3-diaryl-pyrrolo[1,2-<Emphasis Type="Italic">a</Emphasis>]quinoxalines from 2-(1h-pyrrol-1-yl)phenylamines |
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| Authors: | L M Potikha V A Kovtunenko |
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| Institution: | (1) Department of Mathematics, University of Illinois, Urbana, IL 61801, USA;(2) Department of Mathematics, University of North Carolina, Chapel Hill, NC 27599, USA;(3) Department of Marine Sciences, University of North Carolina, Chapel Hill, NC 27599, USA;(4) CB#3250, Phillips Hall, University of North Carolina, Chapel Hill, NC 27599-3250, USA; |
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| Abstract: | The condensation of 1,3-diaryl-4-bromo-2-buten-1-ones with o-phenylenediamine leads to 2-2,4-diaryl-1H-pyrrol-1-yl]phenylamines.
Heating solutions of these compounds in formic acid leads to formylation and intramolecular condensation to give 1,3-diarylpyrrolo1,2-a]quinoxalines. The acylation of 2-2,4-diphenyl-1H-pyrrol-1-yl]phenylamine with acetic anhydride in acetic acid leads to an
acetamide, which readily cyclizes to give 4-methyl-1,3-diphenylpyrrolo1,2-a]quinoxaline upon heating with POCl3. |
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