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

doi:10.1021/ol301550e

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	3704-3707
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	14
DOIs	https://doi.org/10.1021/ol301550e
State	Published - Jul 20 2012

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry
Biochemistry

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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.",

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T2 - A route to novel quinoxaline-based heterocycles

AU - Shoker, Tharallah A.

AU - Ghattass, Khaled I.

AU - Fettinger, James C.

AU - Kurth, Mark J.

AU - Haddadin, Makhluf J.

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AB - 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.

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