Synthetic Exploration of Oxacalix[2]arene[2]quinazolines

Autor:	Wim Van Rossom, Koen Robeyns, Wouter Maes, Lingam Kishore, Wim Dehaen, Luc Van Meervelt
Rok vydání:	2010
Předmět:	Stereochemistry Organic Chemistry Regioselectivity Electrophilic aromatic substitution Condensation reaction Medicinal chemistry chemistry.chemical_compound chemistry Nucleophilic aromatic substitution Calixarene Quinazoline Nucleophilic substitution Physical and Theoretical Chemistry Cyclophane
Zdroj:	European Journal of Organic Chemistry. 2010:4122-4129
ISSN:	1434-193X
DOI:	10.1002/ejoc.201000460
Popis:	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 frag-ment-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. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Databáze:	OpenAIRE
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