title: Regioselective syntheses, structural characterization, and electron ionization mass spectrometric behavior of regioisomeric 2,3-disubstituted 2-imino-1,3-thiazolidin-4-ones.
abstract: The regioselective syntheses of 3-alkyl(aryl)-2-(anthracen-9'-ylimino)-1,3-thiazolidin-4-ones (2) and 2-alkyl(aryl)imino-3-(anthracen-9'-yl)-1,3-thiazolidin-4-ones (3) from N-(anthracen-9-yl)-N'-alkyl(aryl)thioureas were accomplished effectively using methyl bromoacetate and bromoacetyl bromide, respectively. Detailed structural characteristics were confirmed mainly by NMR techniques. The mass spectrometric behavior of the resulting sets of compounds of known structures was shown to be characteristic for each set. Some interesting fragmentation pathways involving the transfer and rearrangements of various moieties were also revealed, as well as regioisomerization for particular substituent-specific fragmentations.
authors.affiliation: Structural Chemistry Group, Department of Chemistry, University of Turku, FIN-20014 Turku, Finland.
authors.forename: Karel D
authors.initials: KD
authors.lastname: Klika
authors.forename: Pauliina
authors.initials: P
authors.lastname: Valtamo
authors.forename: Ladislav
authors.initials: L
authors.lastname: Janovec
authors.forename: Gejza
authors.initials: G
authors.lastname: Suchár
authors.forename: Pavol
authors.initials: P
authors.lastname: Kristian
authors.forename: Ján
authors.initials: J
authors.lastname: Imrich
authors.forename: Henri
authors.initials: H
authors.lastname: Kivelä
authors.forename: Juraj
authors.initials: J
authors.lastname: Alföldi
authors.forename: Kalevi
authors.initials: K
authors.lastname: Pihlaja
mesh_terms: D000873:Anthracenes / Q000737:chemistry; D003198:Computer Simulation; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D008970:Molecular Weight; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D013237:Stereoisomerism; D045162:Thiazolidinediones / Q000032:analysis* / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000873:Anthracenes; D045162:Thiazolidinediones