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Chemical Research in Chinese Universities ›› 2012, Vol. 28 ›› Issue (6): 994-998.

• Articles • Previous Articles     Next Articles

Facile Syntheses of 3-Isopentenyl Flavone and 3-Geranyl Flavone

HUANG Chu-sheng1, SHI Jian-cheng1, LIU Hong-xing1, CHEN Qian1, DUAN Hong-xia2   

  1. 1. College of Chemistry and Life Sciences, Guangxi Teachers Education University, Nanning 530001, P. R. China;
    2. Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, P. R. China
  • Received:2012-01-10 Revised:2012-06-04 Online:2012-11-25 Published:2012-11-09
  • Contact: HUANG Chu-sheng E-mail:wsf668@sina.cn
  • Supported by:

    Supported by the National Natural Science Foundation of China(No.20062001) and the Natural Science Foundation of Guangxi Zhuang Autonomous Region, China(Nos.0991009 and 0447036).

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Abstract:

Although there was a strong steric effect, isopentenyl and geranyl moieties were successfully introduced into C3 position in flavone skeleton so as to synthesize the 3-isopentenyl flavone and 3-geranyl flavone under two cyclization conditions(AcOH/HCl and concentrated H2SO4/MeOH) in this report. It was found that the optimum cyclization conditions for 3-isopentenyl flavone and 3-geranyl flavone were, respectively, AcOH/HCl and H2SO4/MeOH. Furthermore, the donating electron ability is in the sequence 3-geranyl flavone>3-isopentenyl flavone according to the density functional theory(DFT) calculations, suggesting the longer alkyl chain at 3-position would be more favorable for enhancing the donating electron ability. The present synthetic routes might reveal potential applicability in our continued studies on the total syntheses of other natural 3-alkyl flavonoids.

Key words: 3-Isopentenyl flavone, 3-Geranyl flavone, 3-Alkyl flavonoid