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Synthetic Exploration of Oxacalix[2]arene[2]quinazolines
Author(s) -
Van Rossom Wim,
Kishore Lingam,
Robeyns Koen,
Van Meervelt Luc,
Dehaen Wim,
Maes Wouter
Publication year - 2010
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.201000460
Subject(s) - chemistry , nucleophilic substitution , quinazoline , nucleophilic aromatic substitution , solid state , nucleophile , stereochemistry , substitution (logic) , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , computer science , programming language
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.