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Synthesis and DFT calculations of mono‐ and di‐methylated cucurbit[7]uril based on imidazole derivatives.
- Source :
-
Journal of Heterocyclic Chemistry . Dec2023, Vol. 60 Issue 12, p2072-2080. 9p. - Publication Year :
- 2023
-
Abstract
- Nowadays, functionalized cucurbit[n]urils are considered one of the most important examples of macromolecules and have attracted a lot of attention due to their potential applications in several sectors. In the present work monomethyl‐cucurbit[7]uril (3) was synthesized for the first time through facile synthetic route with high purity form by the reaction of monomethylglycoluril (3a‐methyltetrahydroimidazo[4,5‐d]imidazole‐2,5(1H,3H)‐dione) with glycoluril (tetrahydroimidazo[4,5‐d]imidazole‐2,5(1H,3H)‐dione) in the ratio of 1:6, respectively, and formaldehyde in the presence of hydrochloric acid as a catalyst for 24 h at 95°C through Mannich reaction. Moreover, dimethyl‐cucurbit[7]uril (5) was successfully synthesized through the reaction of dimethylglycoluril (3a,6a‐dimethyltetrahydroimidazo[4,5‐d]imidazole‐2,5(1H,3H)‐dione) with glycoluril (tetrahydroimidazo[4,5‐d]imidazole‐2,5(1H,3H)‐dione), following the same procedure as for the monomethyl‐cucurbit[7]uril. The chemical structures of the obtained compounds were established by mass spectrometry, NMR spectroscopy, and quantum‐chemical calculations. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 0022152X
- Volume :
- 60
- Issue :
- 12
- Database :
- Academic Search Index
- Journal :
- Journal of Heterocyclic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 173969768
- Full Text :
- https://doi.org/10.1002/jhet.4738