Synthesis and enantiomeric recognition studies of optically active acridone bis(urea) and bis(thiourea) derivatives. Issue 23 (15th December 2015)

• Record Type: Journal Article
• Authors: Pál, Dávid; Móczár, Ildikó; Kormos, Attila; Baranyai, Péter; Óvári, László; Huszthy, Péter
• Is Part Of: Tetrahedron, asymmetry. Volume 26:Issue 23(2015)
• Page Start: 1335
• Page End: 1340
• Publication Date: 2015-12-15
• Subjects: Asymmetry (Chemistry) -- Periodicals; 547.005
• DOI: 10.1016/j.tetasy.2015.10.004
• Languages: English
• ISSNs: 0957-4166

Abstract

Graphical abstract: Abstract: Novel optically active acridone bis(urea) and bis(thiourea) derivatives were synthesized and their enantiomeric recognition abilities towards the enantiomers of tetrabutylammonium salts of α-hydroxy and N -protected α-amino acids were examined in acetonitrile–DMSO 99:1 using fluorescence spectroscopy. Abstract : 1, 1′-(9-Oxo-9, 10-dihydroacridine-4, 5-diyl)bis{3-[(1 S )-1-phenylethyl]urea}: C31 H29 N5 O3 Ee ⩾ 96% [ α ]D 25 = −28 ( c 0.15, DMF) Source of chirality: ( S )-1-phenylethyl isocyanate Absolute configuration: ( S, S ) Abstract : 1, 1′-(9-Oxo-9, 10-dihydroacridine-4, 5-diyl)bis{3-[(1 S )-1-phenylethyl]thiourea}: C31 H29 N5 OS2 Ee ⩾ 96% [ α ]D 25 = −21 ( c 0.15, DMF) Source of chirality: ( S )-1-phenylethyl isothiocyanate Absolute configuration: ( S, S )