One-Pot Synthesis of 4-Substituted 3-Amino-2-cyanothiophenes Involving O-Ethyl Thioformate

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• 作者：Haiming Zhang ; Mark S. Bednarz ; Ngiap-Kie Lim ; Gonzalo Hernandez ; Wenxue Wu
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：May 2, 2014
• 年：2014
• 卷：16
• 期：9
• 页码：2522-2525
• 全文大小：292K
• 年卷期：v.16,no.9(May 2, 2014)
• ISSN：1523-7052

文摘

An efficient one-pot synthesis of 4-substituted 3-amino-2-cyanothiophenes is described. Treatment of 2-alkyl or aryl substituted acetonitrile sequentially with 2.1 equiv of LDA, 1.1 equiv of O-ethyl thioformate, and 1.2 equiv of 2-chloroacetonitrile afforded the thiophenes in moderate to good yields. The thiophene core can be readily incorporated into more elaborate pharmaceutically relevant structures as demonstrated by converting 3-amino-2-cyano-4-phenylthiophene (1g) to various functionalized thieno[3,2-d]pyrimidines in only two steps.