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.doc

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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