Unusual friedlander reactions: A route to novel quinoxaline-based heterocycles

Tharallah A. Shoker, Khaled I. Ghattass, James C. Fettinger, Mark J. Kurth, Makhluf J. Haddadin

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

Acid catalyzed Friedlander reactions of a number of 2,3-dihydro-1H- cyclopenta[b]quinoxaline-1-ones with 2-aminobenzaldehyde yield, unexpectedly, 8H-indolo[3,2-a]phenazine and quinolino[2,3-c]cyclopentadienone[2,3-b] quinoxalines, the structures of derivatives of which were confirmed by X-ray crystallography. Easy routes to novel quinoxaline-based indoles, quinolones, and quinoxaline-1,4-dioxides are reported, and proposed mechanisms for the unexpected products are discussed.

Original languageEnglish (US)
Pages (from-to)3704-3707
Number of pages4
JournalOrganic Letters
Volume14
Issue number14
DOIs
StatePublished - Jul 20 2012

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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    Shoker, T. A., Ghattass, K. I., Fettinger, J. C., Kurth, M. J., & Haddadin, M. J. (2012). Unusual friedlander reactions: A route to novel quinoxaline-based heterocycles. Organic Letters, 14(14), 3704-3707. https://doi.org/10.1021/ol301550e