The synthesis of 2,2-disubstituted 3-nitrochromenes from salicylaldehyde and 2,2-disubstituted 1-nitroalkenes

Ming Chung Yan, Yeong Jiunn Jang, Wen Yu Kuo, Zhijay Tu, Kao Hsien Shen, Ting Shen Cuo, Chuen Her Ueng, Ching Fa Yao*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

25 引文 斯高帕斯(Scopus)

摘要

Reactions of salicylaldehyde (1) with β-nitrostyrenes (2), (4), and (6) in the presence of 1,4-diazabicyclo[2.2.2] octane (DABCO) without the use of solvent at 40 °C gave high yields of the corresponding 3-nitrochromenes, respectively. Other conjugated nitroalkenes were also used to react with salicylaldehyde under the similar conditions and the yields of substituted 3-nitrochromenes were moderate to high. 96% of cis-3-nitro-4-hydroxyflavane (11) was isolated as sole stereoisomer when 1 reacted with 2-nitromethyleneadamantane (10) under similar condition. When the reaction temperature was increased to 90 °C, 11 underwent dehydration to generate 74% of the corresponding 3-nitrochromene (12).

原文英語
頁(從 - 到)1033-1048
頁數16
期刊Heterocycles
57
發行號6
DOIs
出版狀態已發佈 - 2002 6月 1

ASJC Scopus subject areas

  • 分析化學
  • 藥理
  • 有機化學

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