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

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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.

Original languageEnglish
Pages (from-to)1565-1570
Number of pages6
JournalJournal of Organic Chemistry
Volume69
Issue number5
DOIs
Publication statusPublished - 2004 Mar 5

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ASJC Scopus subject areas

  • Organic Chemistry

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