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Paper | Regular issue | Vol 71, No. 10, 2007, pp.2211-2218
Published online, 10th July, 2007
DOI: 10.3987/COM-07-11116
Synthesis and Structure of Thiacalix[4]arene Derivatives Bearing Thiazole Functional Groups at Lower Rims

Bang-Tun Zhao,* Zhen Zhou, and Zhen-Ning Yan*

*Department of Chemistry, Luoyang Normal University, Luoyang 471022, China

Abstract

The p-tert-butylthiacalix[4]arene (1) was firstly alkylated with 1, 3-dibromopropane and 1,4-dibromobutane to give thiacalix[4]arene derivatives (2a and 2b) in the presence of potassium carbonate, respectively. A series of p-tert-butylthiacalix[4]arene derivatives (3a, 3b, 4a, 4b) which append thiadiazole groups at the lower rims were easily synthesized in good yields by the reaction of tetrabromoalkoxythiacalix[4]arene intermediates 2 with 2-mercaptothiadiazole compounds in the presence of potassium carbonate. All new compounds were characterized by 1H NMR, 13C NMR, IR, MS, elemental analysis and X-ray diffraction on single crystals of 2b, 3b.