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Updated: Jul 6, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Oxyfunctionalization of calixarene quinone rings
Francesco Troisi1, Lucia Citro, Carmine Gaeta
1Dipartimento di Chimica, Università di Salerno, Via Ponte don Melillo, I-84084 Fisciano (Salerno), Italy.
Epoxidation of calixquinones introduces oxygenated groups, forming cis-diepoxy-p-dione structures. Subsequent reduction yields novel calixarene hybrids with dianhydroinositol units, expanding the calixcyclitol family.
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Calixarenes are versatile macrocyclic compounds with tunable properties.
- Functionalization of calixarene walls is crucial for developing new molecular architectures.
Purpose of the Study:
- To explore the epoxidation of calixquinone rings for introducing oxygenated functionalities.
- To synthesize and characterize novel hybrid calixarenes containing dianhydroinositol moieties.
Main Methods:
- Epoxidation of calixquinones.
- Carbonyl reduction of epoxidized calixquinones.
- 2D NMR spectroscopy for structural elucidation.
- Molecular mechanics (MM3) calculations.
- X-ray crystallography.
Main Results:
- Successful epoxidation of quinone rings in calixquinones.
- Formation of cis-diepoxy-p-dione moieties within the calixarene framework.
- Synthesis of hybrid calixarenes with dianhydroinositol (calixinositol) units.
- Determination of regio- and stereochemistry of the synthesized compounds.
Conclusions:
- Epoxidation of calixquinones is an effective strategy for functionalizing calixarene walls.
- The synthesized calixinositols represent a new class of calixcyclitols.
- Combined spectroscopic, computational, and crystallographic methods confirm the structures.
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