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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.

Authors
  • Yan, Ming-Chung
  • Tu, Zhijay
  • Lin, Chunchi
  • Ko, Shengkai
  • Hsu, Jianming
  • Yao, Ching-Fa
Type
Published Article
Journal
The Journal of organic chemistry
Publication Date
Mar 05, 2004
Volume
69
Issue
5
Pages
1565–1570
Identifiers
PMID: 14987012
Source
Medline
License
Unknown

Abstract

2-Aryl-3-nitro-1,2-dihydroquinolines 3 were prepared from the reaction of beta-nitrostyrenes 2 and 2-aminobenzaldehyde 1 in the presence of DABCO. Not only beta-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 beta-nitrostyrenes 2, unique rearrangement products were produced.

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