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 Citations (Scopus)

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

Fingerprint

quinoxalines
Quinoxalines
routes
Indoles
X ray crystallography
X Ray Crystallography
Quinolones
indoles
dioxides
crystallography
Derivatives
Acids
acids
products
x rays

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

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

Unusual friedlander reactions : A route to novel quinoxaline-based heterocycles. / Shoker, Tharallah A.; Ghattass, Khaled I.; Fettinger, James C.; Kurth, Mark J.; Haddadin, Makhluf J.

In: Organic Letters, Vol. 14, No. 14, 20.07.2012, p. 3704-3707.

Research output: Contribution to journalArticle

Shoker, TA, Ghattass, KI, Fettinger, JC, Kurth, MJ & Haddadin, MJ 2012, 'Unusual friedlander reactions: A route to novel quinoxaline-based heterocycles', Organic Letters, vol. 14, no. 14, pp. 3704-3707. https://doi.org/10.1021/ol301550e
Shoker TA, Ghattass KI, Fettinger JC, Kurth MJ, Haddadin MJ. Unusual friedlander reactions: A route to novel quinoxaline-based heterocycles. Organic Letters. 2012 Jul 20;14(14):3704-3707. https://doi.org/10.1021/ol301550e
Shoker, Tharallah A. ; Ghattass, Khaled I. ; Fettinger, James C. ; Kurth, Mark J. ; Haddadin, Makhluf J. / Unusual friedlander reactions : A route to novel quinoxaline-based heterocycles. In: Organic Letters. 2012 ; Vol. 14, No. 14. pp. 3704-3707.
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