The Synthesis and Properties of the First Representatives of Hydroxy-Substituted Azacrownophanes and Cryptand with 2,7-Dihydroxyfluorenone Fragments

Alexander V. Lobach, Irene S. Yakovenko, and Tatyana I. Kirichenko^@

A.V. Bogatskiy Physico-Chemical Institute, National Academy of Sciences of Ukraine, 65080 Odessa, Ukraine

^@Corresponding author E-mail: ti-kirichenko@rambler.ru

The condensation of diglycidyl ethers of 2,7-dihydroxy-, 2,7-bis(2-hydroxyethoxy)- and 2,7-bis[2-(2-hydroxyethoxy)ethoxy]fluorenones with benzylamine in EtOH or EtOH:THF (1:1) under high dilution conditions has led to the first representatives of dihydroxyfluorenono-azaсrownophanes and tetrahydroxybis(fluorenone)diazacrownophanes. These compounds are the products of [1+1] or [2+2] cyclization in 15–35 % yields. Similar condensation of 2,7-bis[2-(2-hydroxyethoxy)ethoxy]fluorenone with diaza-18-crown-6 in ethanol dihydroxyfluorenonocryptand led to 28 % yield. The resulting compounds were isolated as mixtures of D,L- and meso-diastereoisomers in 1:1 and 1:2:1 ratios.

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The Synthesis and Properties of the First Representatives of Hydroxy-Substituted Azacrownophanes and Cryptand with 2,7-Dihydroxyfluorenone Fragments

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