Issue 7, 2017

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
21 3 2017
Accepted
24 4 2017
First published
28 4 2017

Org. Chem. Front., 2017,4, 1425-1429

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements