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. Author manuscript; available in PMC: 2013 Aug 28.
Published in final edited form as: Aust J Chem. 2012 Jul 10;65(10):1396–1404. doi: 10.1071/CH12140

Scheme 1.

Scheme 1

Synthesis of 4-iminothiazolidin-2-ones. Reagents and conditions: (a) Piperonal (0.56 equiv), β-alanine (1 equiv), CH3CO2H, reflux, 3 h, 100 %. (b) 1,4-Dioxane, P2S5 (0.36 equiv), reflux, 2.5 h, 56 %. (c) MeI (5 equiv), N-methyl-2-pyrrolidinone, N,N-diisopropylethylamine (1.15 equiv), room temp., 2 h, 87 %. (d) NH2R (1–5 equiv), MeOH or EtOH, reflux, 18 h, 100 %. (e) 1 N NaOH/ethanol (1 : 2, 7.5 mL), reflux, 5 h, 39 %.