Abstract
We report the alkoxylation of methyl-substituted quinoxalino[2,3-c] cinnolines to give acetals and orthoesters in high yields. Routes to the precursors of this alkoxylation reaction as well as other quinoxalino[2,3-c] cinnoline and their 5-oxide derivatives are reported. Most of these quinoxalino[2,3-c]cinnolines were prepared by cyclization of the corresponding 2-amino-3-(2-nitrophenyl)quinoxaline, which, in turn, result from an unusual Beirut reaction from benzofurazan oxides plus 2-nitrobenzylcyanides. Mechanistic explanations for these intriguing reactions are presented.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 8421-8427 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 76 |
| Issue number | 20 |
| DOIs | |
| State | Published - Oct 21 2011 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Quinoxalino[2,3- c ]cinnolines and their 5- N -oxide : Alkoxylation of methyl-substituted quinoxalino[2,3- c ]cinnolines to acetals and orthoesters. / Haddadin, Makhluf J.; El-Khatib, Mirna; Shoker, Tharallah A.; Beavers, Christine M.; Olmstead, Marilyn M.; Fettinger, James C.; Farber, Kelli M.; Kurth, Mark J.
In: Journal of Organic Chemistry, Vol. 76, No. 20, 21.10.2011, p. 8421-8427.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Quinoxalino[2,3- c ]cinnolines and their 5- N -oxide
T2 - Alkoxylation of methyl-substituted quinoxalino[2,3- c ]cinnolines to acetals and orthoesters
AU - Haddadin, Makhluf J.
AU - El-Khatib, Mirna
AU - Shoker, Tharallah A.
AU - Beavers, Christine M.
AU - Olmstead, Marilyn M.
AU - Fettinger, James C.
AU - Farber, Kelli M.
AU - Kurth, Mark J.
PY - 2011/10/21
Y1 - 2011/10/21
N2 - We report the alkoxylation of methyl-substituted quinoxalino[2,3-c] cinnolines to give acetals and orthoesters in high yields. Routes to the precursors of this alkoxylation reaction as well as other quinoxalino[2,3-c] cinnoline and their 5-oxide derivatives are reported. Most of these quinoxalino[2,3-c]cinnolines were prepared by cyclization of the corresponding 2-amino-3-(2-nitrophenyl)quinoxaline, which, in turn, result from an unusual Beirut reaction from benzofurazan oxides plus 2-nitrobenzylcyanides. Mechanistic explanations for these intriguing reactions are presented.
AB - We report the alkoxylation of methyl-substituted quinoxalino[2,3-c] cinnolines to give acetals and orthoesters in high yields. Routes to the precursors of this alkoxylation reaction as well as other quinoxalino[2,3-c] cinnoline and their 5-oxide derivatives are reported. Most of these quinoxalino[2,3-c]cinnolines were prepared by cyclization of the corresponding 2-amino-3-(2-nitrophenyl)quinoxaline, which, in turn, result from an unusual Beirut reaction from benzofurazan oxides plus 2-nitrobenzylcyanides. Mechanistic explanations for these intriguing reactions are presented.
UR - http://www.scopus.com/inward/record.url?scp=80054108288&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=80054108288&partnerID=8YFLogxK
U2 - 10.1021/jo201687x
DO - 10.1021/jo201687x
M3 - Article
C2 - 21905671
AN - SCOPUS:80054108288
VL - 76
SP - 8421
EP - 8427
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 20
ER -