Synthesis of Cucurbit[6]uril Using 1-Hydroxyethylidene-1,1-Diphosphonic Acid as a “Green Catalyst”
Кукурбит6урилдің синтезі 1-гидроксиэтан-1,1-дифосфон қышқылын «жасыл катализатор» ретінде пайдалану
Синтез кукурбит6урила с использованием 1-гидроксиэтан-1,1-дифосфоновой кислоты в качестве «зеленого» катализатора
Panshina S.Y. Bakibaev A.A. Guslyakov A.N. Malkov V.S.
2022E.A.Buketov Karaganda State University Publish House
Bulletin of the Karaganda University Chemistry Series
2022#108Issue 45 - 13 pp.
Glycoluril (2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione) and its derivatives have a special place in chemistry of heterocyclic compounds. The macrocyclic derivatives of glycoluril, namely cucurbit[n]urils have recently attracted the greatest interest due to their unique properties. Cucurbit[n]urils are usually synthesized by the condensation reaction of glycoluril with paraformaldehyde using strong mineral acids as a catalyst. In this work, 1-hydroxyethylidene-1,1-diphosphonic acid (HEDP) was used for the first time as a catalyst for “Green chemistry” in the synthesis of cucurbit[6]uril in an aqueous medium. The reaction of glycoluril and paraformaldehyde in a ratio of 1: 2 with two equivalents of 1-hydroxyethylidene-1,1-diphosphonic acid as a catalyst was carried out, in which the hexamer of cucurbituril (n = 6) was obtained in 25 % yield. The clathrate of cucurbit[6]uril with acetone was obtained by treating the cucurbituril hexamer with acetone. The reaction of glycoluril with paraformaldehyde in the presence of HEDP can be used as a competitive method for the synthesis of cucurbit[6]uril. The structures of the obtained compounds were proven by NMR and IR spectroscopy methods. The phase composition of isolated crystals of cucurbit[6]uril hydrate was analyzed by the powder X-ray diffraction (XRD).
1-diphosphonic acid , 1-hydroxyethylidene-1 , cucurbit[6]uril , glycoluril , NMR , oligomer , paraformaldehyde , “Green” catalyst , “guest-host” interactions
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Department of Organic Chemistry and Polymers, Karagandy University of the name of academician E.A. Buketov, Universitetskaya street, 28, Karaganda, 100024, Kazakhstan
Laboratory of Organic Synthesis, National Research Tomsk State University, Lenin str., 36, Tomsk, 634050, Russian Federation
Chemical Sciences, The Laboratory of Organic Synthesis, National Research Tomsk State University, Lenin str., 36, Tomsk, 634050, Russian Federation
Department of Organic Chemistry and Polymers
Laboratory of Organic Synthesis
Chemical Sciences
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