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A Novel and Versatile Entry to Asymmetrically Substituted Pyrazines

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journal contribution
posted on 21.03.2008, 00:00 by Vaibhav Pravinchandra Mehta, Anuj Sharma, Kristof Van Hecke, Luc Van Meervelt, Erik Van der Eycken
A novel and convenient procedure for the synthesis of asymmetrically tri- and tetrasubstituted pyrazines starting from para-methoxybenzyl-protected 3,5-dichloro-2(1H)-pyrazinones was elaborated. The key step is the conversion of the intermediate para-methoxybenzyl-protected thiopyrazinone upon treatment with MeI/I2, into a pyrazine, rendering the chlorine in the C5-position susceptible to substitution. This approach entails the orthogonal introduction of the four substituents of the pyrazine scaffold. The application of microwave irradiation during different steps of the sequence has been shown to be highly valuable for speeding up reactions.