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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