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

Department of Chemistry

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

44 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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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 › 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.",

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AU - Tu, Zhijay

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AU - Hsu, Jianming

AU - Yao, Ching Fa

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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

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