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 …

MC Yan, Z Tu, C Lin, S Ko, J Hsu…

Index: Yan, Ming-Chung; Tu, Zhijay; Lin, Chunchi; Ko, Shengkai; Hsu, Jianming; Yao, Ching-Fa Journal of Organic Chemistry, 2004 , vol. 69, # 5 p. 1565 - 1570

Full Text: HTML

Citation Number: 34

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- ...