Synthesis and enantiomeric recognition studies of optically active acridone bis(urea) and bis(thiourea) derivatives

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.

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1,1′-(9-Oxo-9,10-dihydroacridine-4,5-diyl)bis{3-[(1S)-1-phenylethyl]urea}C31H29N5O3Ee ⩾ 96%[α]D25 = −28 (c 0.15, DMF)Source of chirality: (S)-1-phenylethyl isocyanateAbsolute configuration: (S,S)

1,1′-(9-Oxo-9,10-dihydroacridine-4,5-diyl)bis{3-[(1S)-1-phenylethyl]thiourea}C31H29N5OS2Ee ⩾ 96%[α]D25 = −21 (c 0.15, DMF)Source of chirality: (S)-1-phenylethyl isothiocyanateAbsolute configuration: (S,S)