One-Pot Multicomponent Domino Synthesis of 4-Aminothiazole-2(3H)-thiones

Abstract

A new multicomponent domino reaction has been developed for the synthesis of 4-aminothiazole-2(3H)-thiones. Carbon disulfide was successfully used in the preparation of 4-aminothiazole-2(3H)-thione derivatives through reaction with primary amines and 2-bromo-2-arylacetonitriles in the presence of sodium carbonate and a catalytic amount of sodium iodide.

Key words

amines - catalysis - heterocycles - multicomponent reactions - domino reactions - cyclizations

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• 18 4-Aminothiazole-2(3H)-thiones 3a–n; General ProcedureNa₂CO₃ (1.2 mmol, 128 mg) and NaI (0.5 mmol, 75 mg) were added to a mixture of the appropriate aryl(bromo)acetonitrile (1 mmol), primary amine (1mmol), and CS₂ (1.2 mmol, 73 µL) in EtOH (5 mL), and the mixture was stirred at r.t. for 10 min while the progress of the reaction was monitored by TLC (hexane–EtOAc, 5:1). When the reaction was complete, the mixture was filtered and concentrated in vacuo to give a crude product that was purified by recrystallization from a suitable solvent to afford the pure product as a yellow solid.