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

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 K(2)CO(3) in refluxing ethanol is described. This transformation generates two C–C bonds in a single o...

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Detalles Bibliográficos
Autores principales: Vivek Kumar, Sundaravel, Muthusubramanian, Shanmugam, Menéndez, J Carlos, Perumal, Subbu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4660920/
https://www.ncbi.nlm.nih.gov/pubmed/26664589
http://dx.doi.org/10.3762/bjoc.11.185
Descripción
Sumario: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 K(2)CO(3) 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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