Regioselective syntheses, structural characterization, and electron ionization mass spectrometric behavior of regioisomeric 2,3-disubstituted 2-imino-1,3-thiazolidin-4-ones.
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.
Klika
Karel D
KD
Structural Chemistry Group, Department of Chemistry, University of Turku, FIN-20014 Turku, Finland.
Valtamo
Pauliina
P
Janovec
Ladislav
L
Suchár
Gejza
G
Kristian
Pavol
P
Imrich
Ján
J
Kivelä
Henri
H
Alföldi
Juraj
J
Pihlaja
Kalevi
K
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*
D000873:Anthracenes; D045162:Thiazolidinediones