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Synthesis 2009(14): 2341-2344  
DOI: 10.1055/s-0029-1217392
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Improved Synthesis of 1,4,7-Triazacyclononanes (tacns) and 1,4,7,10-Tetraazacyclododecanes (cyclens)

Jianying Huang, Zhongyuan Zhou, Tak Hang Chan*
Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Hong Kong, P. R. of China
Fax: +852 23649932; e-Mail: bcchanth@polyu.edu.hk;
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Publication History

Received 10 March 2009
Publication Date:
08 June 2009 (online)

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An Improved Synthesis of 1,4,7-Triazacyclononanes (tacns) and 1,4,7,10-Tetraazacyclododecanes (cyclens)Synthesis 2010; 2010(22): 3941-3942
DOI: 10.1055/s-0030-1258316

Abstract

Reaction of tosylbis[2-(tosyloxy)ethyl]amine with ethylenediamine gives 1-tosyl-1,4,7-triazacyclononane in good yield. A similar reaction of tosylbis[2-(tosyloxy)ethyl]amine with diethyl­enetriamine gives 1-tosyl-1,4,7,10-tetraazacyclododecane. These tosylated compounds can be further transformed to give 1,4,7-tri­aza­cyclononane (tacn) or 1,4,7,10-tetraazacyclododecane (cyclen) or their derivatives.

Key words

cyclic amines - cyclizations - detosylation - macrocycles - methylations

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