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Regiospecific synthesis, structure and electron ionization mass spectra of 1,3‐thiazolidin‐4‐ones containing the acridine skeleton
Author(s) -
Géci Imrich,
Imrich Ján,
Kristian Pavol,
Kivelä Henri,
Valtamo Pauliina,
Pihlaja Kalevi
Publication year - 2005
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570420524
Subject(s) - chemistry , alkyl , regioselectivity , acridine , aryl , bromide , mass spectrum , mass spectrometry , stereochemistry , medicinal chemistry , organic chemistry , chromatography , catalysis
The synthesis of regioisomeric 3‐alkyl(aryl)‐2‐(acridin‐9′‐yl)imino‐1,3‐thiazolidin‐4‐ones ( 8b‐i ) and 2‐alkyl(aryl)imino‐3‐(acridin‐9′‐yl)‐1,3‐thiazolidin‐4‐ones ( 11a‐i ) was performed by the reaction of 3‐(acridin‐9‐yl)‐1‐alkyl(aryl)thioureas 5a‐i with methyl bromoacetate and bromoacetyl bromide, respectively, via the corresponding isothiourea hydrobromides with excellent regioselectivity. The structure, NMR spectra and mass spectrometric behavior of the resulting compounds are discussed.