Abstract
2-Aryl-3-nitro-1,2-dihydroquinolines 3 were prepared from the reaction of β-nitrostyrenes 2 and 2-aminobenzaldehyde 1 in the presence of DABCO. Not only β-nitrostyrenes but other alkyl nitro olefins also can be used in this reaction as well. When DDQ or silica gel was added to a solution of 3-nitro-1,2-dihydroquinolines 3, 3-nitro-2-substituted-quinolines 4 were obtained. When 2-aminobenzaldehyde derivatives 7 and 12 were reacted with β-nitrostyrenes 2, unique rearrangement products were produced.
| Original language | English |
|---|---|
| Pages (from-to) | 1565-1570 |
| Number of pages | 6 |
| Journal | Journal of Organic Chemistry |
| Volume | 69 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - 2004 Mar 5 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
An Investigation of the Reaction of 2-Aminobenzaldehyde Derivatives with Conjugated Nitro-olefins : An Easy and Efficient Synthesis of 3-Nitro-1,2-dihydroquinolines and 3-Nitroquinolines. / Yan, Ming Chung; Tu, Zhijay; Lin, Chunchi; Ko, Shengkai; Hsu, Jianming; Yao, Ching Fa.
In: Journal of Organic Chemistry, Vol. 69, No. 5, 05.03.2004, p. 1565-1570.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - An Investigation of the Reaction of 2-Aminobenzaldehyde Derivatives with Conjugated Nitro-olefins
T2 - An Easy and Efficient Synthesis of 3-Nitro-1,2-dihydroquinolines and 3-Nitroquinolines
AU - Yan, Ming Chung
AU - Tu, Zhijay
AU - Lin, Chunchi
AU - Ko, Shengkai
AU - Hsu, Jianming
AU - Yao, Ching Fa
PY - 2004/3/5
Y1 - 2004/3/5
N2 - 2-Aryl-3-nitro-1,2-dihydroquinolines 3 were prepared from the reaction of β-nitrostyrenes 2 and 2-aminobenzaldehyde 1 in the presence of DABCO. Not only β-nitrostyrenes but other alkyl nitro olefins also can be used in this reaction as well. When DDQ or silica gel was added to a solution of 3-nitro-1,2-dihydroquinolines 3, 3-nitro-2-substituted-quinolines 4 were obtained. When 2-aminobenzaldehyde derivatives 7 and 12 were reacted with β-nitrostyrenes 2, unique rearrangement products were produced.
AB - 2-Aryl-3-nitro-1,2-dihydroquinolines 3 were prepared from the reaction of β-nitrostyrenes 2 and 2-aminobenzaldehyde 1 in the presence of DABCO. Not only β-nitrostyrenes but other alkyl nitro olefins also can be used in this reaction as well. When DDQ or silica gel was added to a solution of 3-nitro-1,2-dihydroquinolines 3, 3-nitro-2-substituted-quinolines 4 were obtained. When 2-aminobenzaldehyde derivatives 7 and 12 were reacted with β-nitrostyrenes 2, unique rearrangement products were produced.
UR - http://www.scopus.com/inward/record.url?scp=1442349007&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=1442349007&partnerID=8YFLogxK
U2 - 10.1021/jo030070z
DO - 10.1021/jo030070z
M3 - Article
C2 - 14987012
AN - SCOPUS:1442349007
VL - 69
SP - 1565
EP - 1570
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 5
ER -