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Regiospecific synthesis, structure and electron ionization mass spectra of 1,3-thiazolidin-4-ones containing the acridine skeleton

✍ Scribed by Imrich Géci; Ján Imrich; Pavol Kristian; Henri Kivelä; Pauliina Valtamo; Kalevi Pihlaja

Publisher: Journal of Heterocyclic Chemistry
Year: 2005
Tongue: English
Weight: 448 KB
Volume: 42
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570420524

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✦ Synopsis

Abstract

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.

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