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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

48 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	1565-1570
頁數	6
期刊	Journal of Organic Chemistry
卷	69
發行號	5
DOIs	https://doi.org/10.1021/jo030070z
出版狀態	已發佈 - 2004 3月 5

ASJC Scopus subject areas

有機化學

存取文件

10.1021/jo030070z

其它文件與鏈接

CCDC 243286: Experimental Crystal Structure Determination
Yan, M. (Creator), Tu, Z. (Creator), Lin, C. (Creator), Ko, S. (Creator), Hsu, J. (Creator) & Yao, C. (Creator), Unknown Publisher, 2004
DOI: 10.5517/cc854yh, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc854yh&sid=DataCite
資料集: Dataset
CCDC 243282: Experimental Crystal Structure Determination
Yan, M. (Creator), Tu, Z. (Creator), Lin, C. (Creator), Ko, S. (Creator), Hsu, J. (Creator) & Yao, C. (Creator), Unknown Publisher, 2004
DOI: 10.5517/cc854tc, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc854tc&sid=DataCite
資料集: Dataset
CCDC 243290: Experimental Crystal Structure Determination
Yan, M. (Creator), Tu, Z. (Creator), Lin, C. (Creator), Ko, S. (Creator), Hsu, J. (Creator) & Yao, C. (Creator), Unknown Publisher, 2004
DOI: 10.5517/cc8552n, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc8552n&sid=DataCite
資料集: Dataset

引用此

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 等.
於: Journal of Organic Chemistry, 卷 69, 編號 5, 05.03.2004, p. 1565-1570.

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

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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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AU - Yan, Ming Chung

AU - Tu, Zhijay

AU - Lin, Chunchi

AU - Ko, Shengkai

AU - Hsu, Jianming

AU - Yao, Ching Fa

PY - 2004/3/5

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 243286: Experimental Crystal Structure Determination

CCDC 243282: Experimental Crystal Structure Determination

CCDC 243290: Experimental Crystal Structure Determination

引用此