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Bambusurils Bearing Nitro Groups and Their Further Modifications
Author(s) -
Yawer Mirza Arfan,
Sleziakova Kristina,
Pavlovec Lukas,
Sindelar Vladimir
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701329
Subject(s) - chemistry , nitro , condensation , solubility , urea , bearing (navigation) , group (periodic table) , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , alkyl , physics , cartography , thermodynamics , geography
Bambusurils are recently developed neutral anion receptors that show a high affinity towards many inorganic anions, not only in organic solvents but also in water. However, the number of water‐soluble bambusurils and also those bearing functional groups is very limited. In this paper we report the synthesis of four‐ and six‐membered bambusurils containing eight and twelve nitro groups. All the nitro groups on the bambusuril portals could be transformed into amino functions, which provided the macrocycles with water solubility and allowed their further modification. For example, we have demonstrated the conversion of amino groups on the bambusurils into the corresponding urea‐functionalized bambusuril derivatives. We also report the first example of a bambusuril bearing only two functional groups, which was prepared by the condensation of two different glycolurils.