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

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25 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)1033-1048
Number of pages16
JournalHeterocycles
Volume57
Issue number6
Publication statusPublished - 2002 Jun 1

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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    Yan, M. C., Jang, Y. J., Kuo, W. Y., Tu, Z., Shen, K. H., Cuo, T. S., Ueng, C. H., & Yao, C. F. (2002). The synthesis of 2,2-disubstituted 3-nitrochromenes from salicylaldehyde and 2,2-disubstituted 1-nitroalkenes. Heterocycles, 57(6), 1033-1048.