N-取代的3-硝基噻吩-2-胺的高效合成
An efficient synthesis of N-substituted 3-nitrothiophen-2-amines.
作者信息
Vivek Kumar Sundaravel, Muthusubramanian Shanmugam, Menéndez J Carlos, Perumal Subbu
机构信息
Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University,Madurai - 625021, Tamil Nadu, India.
Departmento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain.
出版信息
Beilstein J Org Chem. 2015 Sep 22;11:1707-12. doi: 10.3762/bjoc.11.185. eCollection 2015.
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.
描述了一种新颖的合成方法，即在碳酸钾存在下，α-硝基烯酮N，S-芳基/烷基氨基缩醛与1,4-二硫杂环己烷-2,5-二醇在回流乙醇中反应，以良好的产率合成3-硝基-N-芳基/烷基噻吩-2-胺。该转化过程在单一操作中生成两个C-C键，推测其反应序列包括2-巯基乙醛的生成、亲核羰基加成、环化和消除步骤。
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