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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 18
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Original Articles

FUNCTIONALIZATION OF CALIX[4]- ARENES AT THE LOWER RIM AND SYNTHESIS OF CALIX[4](AZA)CROWNS

Chuan-Feng Chen LMRSS, Center for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100 080, P. R. China
,
Qi-Yu Zheng LMRSS, Center for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100 080, P. R. China
,
Yan-Song Zheng LMRSS, Center for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100 080, P. R. China
&
Zhi-Tang Huang LMRSS, Center for Molecular Sciences, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100 080, P. R. China
Pages 2829-2836 | Received 21 Nov 2000, Published online: 15 Aug 2006
 
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Abstract

Both a monocalix[4]arene derivative 2 and a biscalix[4]arene 3 were isolated from the products of the reaction of p-tert-butylcalix[4]arene with 1,2-dibromoethane. Treating 2 with 2,6-bis(hydroxymethyl)pyridine, 2-aminophenol or 8-hydroxyquinoline, the calix[4](aza)-crowns 4, 5 or 6 were synthesized, respectively. The 1,3-disubstituted calix[4]arene derivative 8 was obtained by the reaction of p-tert-butylcalix[4]arene with p-nitro(2-chloroacetanilide). Reduction of 8 with NaBH4 gave an open calix[4](diaza)crown compound 9.

ACKNOWLEDGMENT

This work was supported by The National Natural Science Foundation of China.

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