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Synthesis 2001(7): 1023-1026
DOI: 10.1055/s-2001-14562
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Heteroarylazo-substituted Calix[4]arenes

Chuan-Ming Jina, Guo-Yuan Lu*a, Zhen-Sheng Wanga, Xiao-Zeng Youa, Zhong-Hua Wangb, Wei Gongb, Hou-Ming Wub
a Department of Chemistry, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, P. R. China
b State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China
Fax: +86(25)3317761; e-Mail: nnj.lugy@jlonline.com;
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Publication History

Received 15 January 2001
Publication Date:
30 September 2004 (online)

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Abstract

This paper reports a novel method for preparing heteroarylazo- substituted calix[4]arenes, in which heteroaromatic amines were diazotized with isoamyl nitrite in EtONa-EtOH under refluxing conditions. Mono(heteroarylazo)-, bis(heteroarylazo)- and tetrakis(heteroarylazo)-substituted calix[4]arenes were obtained as main product by diazo-coupling in different molar ratio to calix[4]arenes under pH 7-9 in non-aqueous solution at 0-5 °C. Based on the method, eight novel heteroarylazo-substituted calix[4]arenes have been synthesized by diazo-coupling reaction of calix[4]arene with diazonium salt solutions of 4-aminopyridine or 2-aminothiazole.

Key words

calix[4]arene - diazo coupling - isoamyl nitrite - synthesis

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