A one-pot synthesis of 3-nitrothiophene and 3-nitro-2-substituted thiophenes

Add time:08/08/2019    Source:sciencedirect.com

A one-pot approach to the synthesis of 3-nitrothiophene and 3-nitro-2-substituted thiophenes has been developed. Exposure of 1,4-dithane-2,5-diol to nitroacetates or nitroalkenes in the presence of 25% triethylamine and subsequent treatment with molecular sieves and combinations of silica gel or acidic alumina with DDQ or chloranil formed 3-nitrothiophene or a number of 3-nitro-2-substituted thiophenes with complete regiocontrol. A simple work-up procedure removes the requirement for purification by chromatography for most post-synthetic applications.

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