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Issue 7, 2017
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Synthesis and conformational structure of hydrazo-bridged homo calix[2]pyridine[2]triazines

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Abstract

Presented in this paper are the practical synthesis and conformational structure of hydrazo-bridged homo calix[4]arenes. The step-wise fragment coupling method based on the nucleophilic aromatic substitution reaction of 2,6-dihydrazinylpyridine with 6-alkoxy-2,4-dichlorotriazine afforded effectively hydrazo-linked homo calix[2]pyridine[3]triazines. The exhaustive methylation of –NHNH– linkages led to lipophilic macrocycles, while the introduction of a THP-protected triglyme moiety on a triazine ring produced a water soluble hydrazo-bridged homo calix[2]pyridine[2]triazine. The acquired hydrazo-bridged homo calix[4]arenes adopted a cone conformational structure with two nitrogen atoms of the hydrazine linkage forming respectively a conjugation system with pyridine and triazine rings. The unique macrocyclic conformation and multidentate binding sites would render hydrazo-bridged homo calix[2]pyridine[2]triazines powerful hosts in molecular recognition and self-assembly.

Graphical abstract: Synthesis and conformational structure of hydrazo-bridged homo calix[2]pyridine[2]triazines

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Article information


Submitted
21 Mar 2017
Accepted
24 Apr 2017
First published
28 Apr 2017

Org. Chem. Front., 2017,4, 1425-1429
Article type
Research Article

Synthesis and conformational structure of hydrazo-bridged homo calix[2]pyridine[2]triazines

D. Liang and M. Wang, Org. Chem. Front., 2017, 4, 1425
DOI: 10.1039/C7QO00221A

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