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Regioselective syntheses, structural characterization, and electron ionization mass spectrometric behavior of regioisomeric 2,3‐disubstituted 2‐imino‐1,3‐thiazolidin‐4‐ones
Author(s) -
Klika Karel D.,
Valtamo Pauliina,
Janovec Ladislav,
Suchár Gejza,
Kristian Pavol,
Imrich Ján,
Kivelä Henri,
Alföldi Juraj,
Pihlaja Kalevi
Publication year - 2003
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.1290
Subject(s) - chemistry , regioselectivity , aryl , alkyl , bromide , substituent , structural isomer , fragmentation (computing) , electron ionization , stereochemistry , medicinal chemistry , combinatorial chemistry , ionization , organic chemistry , ion , computer science , operating system , catalysis
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. Copyright © 2003 John Wiley & Sons, Ltd.