Reactions of calix[4]arene carboxymethoxy derivatives with 2-aminoalkylbenzimidazoles in the presence of dicyclohexylcarbodiimide and hydroxybenzotriazole afforded a series of p-tert-butylcalix[4]arene derivatives containing on the lower rim N-(2-benzimidazolylalkyl)carbamoylmethoxy fragments. The reaction carried out in the absence of hydroxybenzOtriazole resulted in macrocycles containing one N-(2-benzimidazolylalkyl)carbamoyl fragment and a fragment of N-(acyl)dicyclohexylisourea.
A new procedure has been proposed for the synthesis of mono-and bis(2-aminoethoxy)-p-(tertbutyl)calix [4]arenes from the corresponding mono-and bis[2-(1,3-dioxoisoindol-2-yl)ethoxy]-p-(tert-butyl)-calix[4]arenes.Modification of calixarenes at the lower rim via introduction of amino groups linked to the phenol fragments of the macrocycle through carbon chains with different lengths could give rise to various complexones capable of binding cations, anions, and neutral species, as well as to biologically active substances.A known procedure for the synthesis of 2-aminoethoxy derivatives of p-(tert-butyl)calix [4]arene (І) is based on reaction of the latter with bromoacetonitrile in the presence of potassium carbonate under the conditions ensuring formation of disubstituted products, followed by reduction of the cyano groups with lithium tetrahydridoaluminate [1][2][3]. Derivatives of 2-alkylisoindole-1,3-diones were used to obtain analogous compounds in which the aminoalkoxy fragment includes more than two carbon atoms. In such a way both diand tetra-substituted aminoalkoxy calix[4]arenes were synthesized [4,5]. We have found no published data on the synthesis of aminoethoxy derivatives of p-(tertbutyl)calix[4]arene with the use of N-(2-bromoethyl)-phthalimide as alkylating agent. Therefore, we made an attempt to develop a procedure for the preparation
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