Formation of water-soluble sulfonated azacalix[4]arenes from cyanuric chloride

Jonathan Clayden; Stephen J M Rowbottom; Michael G. Hutchings; Warren J. Ebenezer

doi:10.1016/j.tetlet.2009.04.068

Formation of water-soluble sulfonated azacalix[4]arenes from cyanuric chloride

Jonathan Clayden^*, Stephen J M Rowbottom, Michael G. Hutchings, Warren J. Ebenezer

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

15 Citations (Scopus)

Abstract

Addition of cyanuric chloride 2 (2,4,6-trichlorotriazine) to 4,6-diaminobenzene-1,3-disulfonic acid 1 gives a bis-triazine 3 which may be cyclised with diaminoarenes to yield water-soluble azacalix[4]arenes 5a-d. Alternatively, double substitution of chloride from the bis-triazine 3 yields new bis-triazine derivatives which may likewise be cyclised to functionalised azacalixarenes bearing functionalised side chains.

Original language	English
Pages (from-to)	3923-3925
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	27
Early online date	23 Apr 2009
DOIs	https://doi.org/10.1016/j.tetlet.2009.04.068
Publication status	Published - 8 Jul 2009

Keywords

Calixarene
Cyanuric chloride
Macrocycle
Sulfonic acid
Triazine
Water-soluble

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title = "Formation of water-soluble sulfonated azacalix[4]arenes from cyanuric chloride",

abstract = "Addition of cyanuric chloride 2 (2,4,6-trichlorotriazine) to 4,6-diaminobenzene-1,3-disulfonic acid 1 gives a bis-triazine 3 which may be cyclised with diaminoarenes to yield water-soluble azacalix[4]arenes 5a-d. Alternatively, double substitution of chloride from the bis-triazine 3 yields new bis-triazine derivatives which may likewise be cyclised to functionalised azacalixarenes bearing functionalised side chains.",

keywords = "Calixarene, Cyanuric chloride, Macrocycle, Sulfonic acid, Triazine, Water-soluble",

author = "Jonathan Clayden and Rowbottom, {Stephen J M} and Hutchings, {Michael G.} and Ebenezer, {Warren J.}",

year = "2009",

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doi = "10.1016/j.tetlet.2009.04.068",

language = "English",

volume = "50",

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journal = "Tetrahedron Letters",

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T1 - Formation of water-soluble sulfonated azacalix[4]arenes from cyanuric chloride

AU - Clayden, Jonathan

AU - Rowbottom, Stephen J M

AU - Hutchings, Michael G.

AU - Ebenezer, Warren J.

PY - 2009/7/8

Y1 - 2009/7/8

N2 - Addition of cyanuric chloride 2 (2,4,6-trichlorotriazine) to 4,6-diaminobenzene-1,3-disulfonic acid 1 gives a bis-triazine 3 which may be cyclised with diaminoarenes to yield water-soluble azacalix[4]arenes 5a-d. Alternatively, double substitution of chloride from the bis-triazine 3 yields new bis-triazine derivatives which may likewise be cyclised to functionalised azacalixarenes bearing functionalised side chains.

AB - Addition of cyanuric chloride 2 (2,4,6-trichlorotriazine) to 4,6-diaminobenzene-1,3-disulfonic acid 1 gives a bis-triazine 3 which may be cyclised with diaminoarenes to yield water-soluble azacalix[4]arenes 5a-d. Alternatively, double substitution of chloride from the bis-triazine 3 yields new bis-triazine derivatives which may likewise be cyclised to functionalised azacalixarenes bearing functionalised side chains.

KW - Calixarene

KW - Cyanuric chloride

KW - Macrocycle

KW - Sulfonic acid

KW - Triazine

KW - Water-soluble

UR - http://www.scopus.com/inward/record.url?scp=65549092677&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2009.04.068

DO - 10.1016/j.tetlet.2009.04.068

M3 - Article (Academic Journal)

AN - SCOPUS:65549092677

SN - 0040-4039

VL - 50

SP - 3923

EP - 3925

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 27

ER -

Formation of water-soluble sulfonated azacalix[4]arenes from cyanuric chloride

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