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Synthesis 2009(7): 1195-1203  
DOI: 10.1055/s-0028-1087995
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

2-(Benzoylimino)thiazolidin-4-ones: Formation by an Alternative Ring Closure and Analysis of Rotational Barriers

Hans-Georg Häckera, Paul W. Elsinghorsta, Susanne Michelsa, Jörg Danielsb, Gregor Schnakenburgb, Michael Gütschow*a
a Pharmaceutical Institute, Pharmaceutical Chemistry I, University of Bonn, An der Immenburg 4, 53121 Bonn, Germany
Fax: +49(228)732567; e-Mail: guetschow@uni-bonn.de;
b Institute of Inorganic Chemistry, University of Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany
Further Information

Publication History

Received 23 October 2008
Publication Date:
06 March 2009 (online)

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Abstract

The reactions of N-benzoyl-N′-(o-cyanoaryl)thioureas with ethyl bromoacetate under alkaline conditions led to the form­ation of either fused 2-(alkylsulfanyl)-4-aminopyrimidines or 2-(benzoylimino)-3-(o-cyanoaryl)thiazolidin-4-ones. The accurate application of slightly different reaction conditions allowed us to adjust the balance between the formation of the pyrimidine or thiazolidine heterocycles. Atropisomerism in the 3-(o-cyanoaryl)thiazolidin-4-ones was influenced by the size of the o-cyanoaryl ring, which was investigated by means of NMR measurements and theoretical calculations.

Key words

atropisomerism - ring closure - regioselectivity - thiazolidin-4-ones - DFT calculations

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