AN EFFICIENT SYNTHESIS OF 1,3-DIARYLPYRROLO[1,2-<i>a</i>]QUINOXALINES FROM 2-(1H-PYRROL-1-YL)PHENYLAMINES

Authors

  • Л. М. Потиха Taras Shevchenko Kiev State University, 01033 Kiev
  • В. А. Ковтуненко Taras Shevchenko Kiev State University, 01033 Kiev

DOI:

https://doi.org/10.1007/6455

Keywords:

γ-bromodypnone, 2-(1H-pyrrol-1-yl)phenylamine, N-[2-(1H-pyrrol-1-yl)phenyl]acetamide, pyrrolo[1, 2-<i>a</i>]quinoxaline, polycyclic heterocyclic compounds

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-diarylpyrrolo[1,2-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-diphenylpyrrolo[1,2-a]quinoxaline upon heating with POCl3.

How to Cite
Potikha, L. M.; Kovtunenko, V. A. Chem. Heterocycl. Compd. 2009, 45, 1396. [Khim. Geterotsikl. Soedin. 2009, 1734.]

For this article in the English edition see DOI 10.1007/s10593-010-0439-8

 

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Published

2021-10-07

Issue

No. 11 (2009)

Section

Original Papers