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

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.

SUBMITTER: Vivek Kumar S

PROVIDER: S-EPMC4660920 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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

Vivek Kumar Sundaravel S Muthusubramanian Shanmugam S Menéndez J Carlos JC Perumal Subbu S

Beilstein journal of organic chemistry 20150922

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. ...[more]

PMID: 26664589

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