Synthesis and enantiomeric recognition studies of optically active 5, 5-dioxophenothiazine bis(urea) and bis(thiourea) derivatives. Issue 19 (15th October 2016)

• Record Type: Journal Article
• Authors: Pál, Dávid; Móczár, Ildikó; Kormos, Attila; Baranyai, Péter; Huszthy, Péter
• Is Part Of: Tetrahedron, asymmetry. Volume 27:Issue 19(2016)
• Page Start: 918
• Page End: 922
• Publication Date: 2016-10-15
• Subjects: Asymmetry (Chemistry) -- Periodicals; 547.005
• DOI: 10.1016/j.tetasy.2016.08.002
• Languages: English
• ISSNs: 0957-4166

Abstract

Graphical abstract: Abstract: Novel optically active 5, 5-dioxophenothiazine bis(urea) and bis(thiourea) derivatives were synthesized and their enantiomeric recognition abilities toward the enantiomers of tetrabutylammonium salts of α-hydroxy and N -protected α-amino acids were examined in acetonitrile using fluorescence spectroscopy. Abstract : 1, 1′-(3, 7-Di- tert -butyl-5, 5-dioxo-5, 10-dihydro-5λ 6 -phenothiazine-1, 9-diyl)bis{3-[(1 S )-1-phenylethyl]urea}: C38 H45 N5 O4 S Ee ⩾ 96% [ α ]D 27 = +65.2 ( c 1.00, DMF) Source of chirality: ( S )-1-phenylethyl isocyanate Absolute configuration: ( S, S ) Abstract : 1, 1′-(3, 7-Di- tert -butyl-5, 5-dioxo-5, 10-dihydro-5λ 6 -phenothiazine-1, 9-diyl)bis{3-[(1 S )-1-phenylethyl]thiourea}: C38 H45 N5 O2 S3 Ee ⩾ 96% [ α ]D 32 = +34.3 ( c 0.67, CH2 Cl2 ) Source of chirality: ( S )-1-phenylethyl isothiocyanate Absolute configuration: ( S, S ) Abstract : 1, 1′-(3, 7-Di- tert -butyl-5, 5-dioxo-5, 10-dihydro-5λ 6 -phenothiazine-1, 9-diyl)bis{3-[(1 S )-1-(naphthalen-1-yl)ethyl]urea}: C46 H49 N5 O4 S Ee ⩾ 96% [ α ]D 31 = +38.9 ( c 1.04, DMF) Source of chirality: ( S )-1-(1-naphthyl)ethyl isocyanate Absolute configuration: ( S, S ) Abstract : 1, 1′-(3, 7-Di- tert -butyl-5, 5-dioxo-5, 10-dihydro-5λ 6 -phenothiazine-1, 9-diyl)bis{3-[(1 S )-1-(naphthalen-1-yl)ethyl]thiourea}: C46 H49 N5 O2 S3 Ee ⩾ 96% [ α ]D 29 = +116 ( c 0.71, CH2 Cl2 ) Source of chirality: ( S )-1-(1-naphthyl)ethyl isothiocyanate Absolute configuration: ( S, S )