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Synthesis of 2,5-Pyrrolidinediones by Microwave Heating. A Direct Entry to Fungicides.

Julio A. Seijas*, M. Pilar Vázquez-Tato*, M. Montserrat Martínez and Gonzalo Núñez

Departamento de Química Orgánica. Universidad de Santiago de Compostela. Facultad de Ciencias de Lugo. Aptdo. 280. 27080-Lugo. Spain.

Imide derivatives are associated with various uses both by its biological[1] or industrial[2] properties. Our interest was specially directed towards 2,5-pyrrolidinediones since among them there are fungicides of agricultural use[3],
Our method consists in heating the acid mixed with the amine in a molar ratio 1:1 up to the disappearance of the starting material. Thus, succinic acid (1) was heated with aniline (2a) yielding N-phenylsuccinimide (3a) in 76%; when the amine employed was 2,5-dichloroaniline (2b) the reaction afforded fungicide 3b in 78% yield, and with benzylamine (2c) we obtained a similar yield (78%) of compound 3c.

We compared these reaction conditions with conventional heating, and we found that reaction times were shorter and yields higher with microwaves.

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