Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 21, Pages 4122-4129Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000460
Keywords
Calixarenes; Nitrogen heterocycles; Aromatic substitution; Regioselectivity; Conformation analysis
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Funding
- Fund for Scientific Research - Flanders (FWO)
- Katholieke Universiteit Leuven
- Ministerie voor Wetenschapsbeleid
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Oxacalix[2]arene[2]quinazoline macrocycles were prepared in good yields, as mixtures of syn and anti isomers, through nucleophilic aromatic substitution cyclocondensation reactions of 2,4-dichloroquinazolines and m-dihydroxybenzenes. The macrocyclization conditions were optimized and the isomeric ratio was investigated by means of one-step and fragment-coupling approaches. The oxacalixarene substitution pattern could easily be varied by altering the dichloroquinazolinyl biselectrophilic and dihydroxyaryl bisnucleophilic building blocks. The solid-state (1,3-alternate) conformational behavior and the oxacalix[4]arene cavity size were explored by X-ray diffraction studies.
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