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

Ming Chung Yan; Zhijay Tu; Chunchi Lin; Shengkai Ko; Jianming Hsu; Ching Fa Yao

doi:10.1021/jo030070z

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

Ming Chung Yan
, Zhijay Tu
, Chunchi Lin
, Shengkai Ko
, Jianming Hsu
, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

51 Citations (Scopus)

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	https://doi.org/10.1021/jo030070z
Publication status	Published - 2004 Mar 5

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo030070z

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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. / Yan, Ming Chung; Tu, Zhijay; Lin, Chunchi et al.
In: Journal of Organic Chemistry, Vol. 69, No. 5, 05.03.2004, p. 1565-1570.

Research output: Contribution to journal › Article › peer-review

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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.",

author = "Yan, \{Ming Chung\} and Zhijay Tu and Chunchi Lin and Shengkai Ko and Jianming Hsu and Yao, \{Ching Fa\}",

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month = mar,

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AU - Yan, Ming Chung

AU - Tu, Zhijay

AU - Lin, Chunchi

AU - Ko, Shengkai

AU - Hsu, Jianming

AU - Yao, Ching Fa

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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.

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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

Abstract

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CCDC 243285: Experimental Crystal Structure Determination

CCDC 243284: Experimental Crystal Structure Determination

CCDC 243289: Experimental Crystal Structure Determination

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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

Abstract

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CCDC 243285: Experimental Crystal Structure Determination

CCDC 243284: Experimental Crystal Structure Determination

CCDC 243289: Experimental Crystal Structure Determination

Cite this