Secondary Amine Derivatives of p-tert-Butyl Thiacalix[4]arenes: Synthesis and Molecular Recognition of Phthalic Acid

Abstract

New tetrasubstituted p-tert-butylthiacalix[4]arenes containing 2-, 3-, and 4-picolylamine fragments at the lower rim in 1,3-alternate conformation were synthesized. It was shown that the macrocycles synthesized are able to bind selectively phthalic acid in the series of dicarboxylic (oxalic, malonic, succinic, adipic, glutaric, fumaric, maleic, isophthalic and terephthalic) and hydroxy (glycolic and tartaric) acids.

Pillar[5]arenes Bearing Amide and Carboxylic Groups as Synthetic Receptors for Alkali Metal Ions

“…As initial compounds for synthesis of pillar [5]arenes containing ten amide fragments, we used macrocycle 3 with ten carboxyl groups. The reaction of the macrocycle 3 (Scheme 1) with a series of tertiary amines (pyrrolidine, [12] morpholine, [23] piperidine), and also with glycine ethyl ester [28] and its dimerglycylglycine ethyl ester [28] was studied. The deca-acid 3 was in situ converted into the deca-acid chloride by reaction with SOCl 2 in the presence of catalytic amounts of DMF.…”

“…[1][2][3][4][5][6] As a rule, a key role in these processes is played by macrocyclic compounds. [7][8][9][10][11][12][13] Depending on the size of the cavity, they are able to form host-guest systems, [14][15][16] leading to the formation of various supramolecular assembles.…”

Selective stepwise oxidation of 1,4-decamethoxypillar[5]arene

“…13 They are employed in organic synthesis, [14][15][16][17][18][19][20] and used as drugs and dyes. 20,21 Development in the chemistry of macrocyclic compounds such as crown ethers, 22,23 cyclodextrins, 24 calixarenes 25 and cucurbiturils, 26 in relation to their ability for molecular recognition of various types of substrates resulted in a number of successes in the construction of biomimetic and supramolecular systems. [27][28][29][30][31] In this regard, the development of easily available methods for the synthesis of macrocycles with different ring sizes, containing one or more 1,4-benzoquinone fragments, may offer new opportunities in the development of a diverse range of materials and bioactive compounds.…”

Towards macrocyclic ionic liquids: novel ammonium salts based on tetrasubstituted p-tert-butylthiacalix[4]arenes

“…Despite large synthetic and conformational diversity of (thia) calix [4]arenes as molecular building platform, [18][19][20][21][22][23][24] there are only few examples of the synthesis of ionic liquids based on them.…”