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  • Title: One-pot synthesis of 4-substituted 3-amino-2-cyanothiophenes involving O-ethyl thioformate.
    Author: Zhang H, Bednarz MS, Lim NK, Hernandez G, Wu W.
    Journal: Org Lett; 2014 May 02; 16(9):2522-5. PubMed ID: 24746285.
    Abstract:
    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.
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