Synthesis and extraction abilities of mono-formylated calix[4]-1,3-aza-crown and its hydrazone derivatives

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• 作者：Fafu Yang (12) yangfafu@fjnu.edu.cn
  Ziyu Jiao (1)
  Zhisheng Huang (1)
  Jianwei Xie (1)
  Hongyu Guo (1)
• 关键词：Calix[4]crown &#8211 ; Biscalix[4]arene &#8211 ; Formylation &#8211 ; Hydrazone &#8211 ; Synthesis &#8211 ; Extraction
• 刊名：Journal of Inclusion Phenomena and Macrocyclic Chemistry
• 出版年：2012
• 出版时间：December 2012
• 年：2012
• 卷：74
• 期：1-4
• 页码：257-263
• 全文大小：399.7 KB
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• 作者单位：1. College of Chemistry and Materials, Fujian Normal University, Fuzhou, 350007 People鈥檚 Republic of China2. Fujian Key Laboratory of Polymer Materials, Fuzhou, 350007 People鈥檚 Republic of China
• ISSN：1573-1111

文摘

By formylation of calix[4]-1,3-aza-crown in hexamethylenetetramine/trifluoroacetic acid system, the first formylated calix[4]-aza-crown derivative 6 was synthesized in yield of 61%. Reacting compound 6 with salicyloyl hydrazine, 2,4-dinitrophenyl hydrazine, nicotinyl hydrazine or phenyl thiosemicarbazide afforded four novel calix[4]crown hydrazone derivatives 7a–d in yields of 70–90%. By condensating compound 6 with series of bifunctional reagents, the novel mono-bridged biscalix[4]-aza-crown hydrazone derivatives 8a–c were prepared in high yields. The extraction experiments showed that all new compounds were good receptors for metal cations, especially, for soft metal cations. The extraction results suggested that the hydrazone groups produced favorable influences for binding soft cations. The two calix[4]arene units in compounds 8a–c could bind metal cations concurrently.