An efficient synthesis of N-substituted 3-nitrothiophen-2-amines

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Abstract

A novel protocol for the synthesis of 3-nitro-N-aryl/alkylthiophen-2-amines in good yields from the reaction of α-nitroketene N,S-aryl/alkylaminoacetals and 1,4-dithiane-2,5-diol in the presence of K2CO3 in refluxing ethanol is described. This transformation generates two C-C bonds in a single operation and presumably proceeds through a reaction sequence comprising 2-mercaptoacetaldehyde generation, nucleophilic carbonyl addition, annelation and elimination steps.

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Kumar, S. V., Muthusubramanian, S., Menéndez, J. C., & Perumal, S. (2015). An efficient synthesis of N-substituted 3-nitrothiophen-2-amines. Beilstein Journal of Organic Chemistry, 11, 1707–1712. https://doi.org/10.3762/bjoc.11.185

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