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 | |
| State | Published - Jul 20 2012 |
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ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
Cite this
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 journal › Article
}
TY - JOUR
T1 - Unusual friedlander reactions
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.
PY - 2012/7/20
Y1 - 2012/7/20
N2 - 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.
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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UR - http://www.scopus.com/inward/citedby.url?scp=84864139405&partnerID=8YFLogxK
U2 - 10.1021/ol301550e
DO - 10.1021/ol301550e
M3 - Article
C2 - 22783916
AN - SCOPUS:84864139405
VL - 14
SP - 3704
EP - 3707
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 14
ER -