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 |
ASJC Scopus subject areas
- Organic Chemistry
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Cite this
Yan, M. C., Tu, Z., Lin, C., Ko, S., Hsu, J., & Yao, C. F. (2004). 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. Journal of Organic Chemistry, 69(5), 1565-1570. https://doi.org/10.1021/jo030070z