Facile Synthesis of 1,6-Bis(2-furyl)-2,5-bis(2-hydroxy-3-formyl-5-methylbenzyl)-2,5-diazahexane a New Dinucleating Ligand.docVIP
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Facile Synthesis of 1,6-Bis(2-furyl)-2,5-bis(2-hydroxy-3-formyl-5-methylbenzyl)-2,5-diazahexane a New Dinucleating Ligand
Molecules 2001, 6, 1001-1005
molecules
ISSN 1420-3049
Facile Synthesis of 1,6-Bis(2-furyl)-2,5-bis(2-hydroxy-3-formyl-5-
methylbenzyl)-2,5-diazahexane: a New Dinucleating Ligand
Gang-Chun Sun
Wang
1
, Zhan-Hang He , Zhong-Jun Li , Xiao-Dong Yuan , Zhi-Juan Yang , Guo-Xi
2 2 3 2
and Chang-Rang Liu
2,*
4
, Liu-Fang Wang
1*
1 National Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou
University, Lanzhou 730000, China; E-mail:sungangchun@371.net.
2 Department of Chemistry, Zhengzhou University, ZhengZhou 450052, China.
3 Department of Applied Oil Engineering, Logistical Engineering University, Chongqing 400042,
China.
4
Department of Chemical Engineering, Anyang University, Anyang 455000, China.
*Author to whom correspondence should be addressed; E-mail: llyyjz@
Received: 15 April 2001; in revised form 29 October 2001 / Accepted: 30 October 2001 / Published:
30 November 2001
_______________________________________________________________________________
Abstract: A convenient three-step preparation of the dinucleating ligand, 1,6-bis(2-
furyl)-2,5-bis(2-hydroxy-3-formyl-5-methylbenzyl)-2,5-diazahexane (3) starting from
2,6-bis(hydroxymethyl)-4-methylphenol (4) is reported. Compound 4 was partially
oxidized with preactivated manganese dioxide to form compound 5, which was converted
to 2-hydroxy-3-chloromethyl-5-ethylbenzaldehyde (6) with conc.HCl/EtOH. Compound
6 in turn reacted with N,N’-bis (2-furyl)-1,2-diaminoethane (7) in the presence of K2CO3
in ethanol to give the title compound 3. No protecting groups were required in the whole
process and the conditions were mild.
Keywords: Synthesis, Dinucleating ligand, 2,5-Diazahexane derivative, Partial
oxididation, Manganese dioxide.
Molecules 2001, 6
1002
Introduction
The design and synthesis of
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