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Trichloroisocyanuric Acid (TCCA) as an efficient homogeneous catalyst for the chemoselective synthesis

Trichloroisocyanuric Acid (TCCA) (1,3,5-trichloro-1,3,5-triazine-2,4,6(1H,3H,5H)-trione or TCCA) is an N-halo compound which has been known since 1902. It has been used primarily as a disinfectant in swimming pools and water treatment. Recently, Trichloroisocyanuric Acid (TCCA) has become attractive candidate as a homogeneous catalyst in organic transformations due to its lack of volatility, commercial availability, low cost and ease of handling. 
Consequently, in continuation of our interest in the synthesis of 2-oxazoline, 2-imidazoline and 2-thiazoline derivatives, the catalytic activity of Trichloroisocyanuric Acid (TCCA)  in this field was investigated. A mixture of a nitrile (l mmol), 2-aminoethanol (6 mmol), ethylenediamine (4 mmol) or 2-aminoethanethiol (1.2 mmol) and TCCA (0.03 mmol for oxazoline, 0.1 mmol for imidazoline and 0.01 mmol for thiazoline synthesis) was stirred at 110 °C for an appropriate time, according to Table I. The reaction was performed under solvent-free conditions. After completion of the reaction, monitored by TLC (eluent: n-hexane:EtOAc, 2:1 for oxazolines and thiazolines, EtOAc:methanol, 10:1 for imidazolines), the reaction mixture was cooled to room temperature and the crude product was purified by column chromatography to afford the pure products in high yields.
High performance liquid chromatography Trichloroisocyanuric Acid (TCCA) in the micro-universe simulated water ecosystems fate, including TCCA in water, sediment organisms (Crown grass, river clams, gibel carp), etc. dynamic changes of the distribution process, enrichment distribution and migration of different phases in different tissues and organisms were studied.