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  • Title: [Novel method for the synthesis of carboxamides from low reactivity esters: synthesis of 2-acylamino-1-benzothiophene-3-carboxamides].
    Author: Bánhegyi P, Wáczek F, Székelyhidi Z, Hegymegi-Barakonyi B, Kéri G, Orfi L.
    Journal: Acta Pharm Hung; 2008; 78(2):75-8. PubMed ID: 18807387.
    Abstract:
    We planned and prepared a kinase inhibitor focused compound library around the 1-benzotiophene core structure, but the 2-acylamino-1-benzotiophene-3-carboxylic acid ethyl ester derivatives could not be converted to amides by the traditional methods like treatment with aqueous or alcoholic ammonia solution or ammonia gas. Under mild reaction conditions we have recovered the starting materials, higher temperature and pressure resulted the formation of pure ring-closed products. We have discovered a new method where the application of lithium amide in tetrahydrofurane resulted the desired compounds in acceptable yields (67-84%). The products were characterized thoroughly by spectral data, elementary analyses and melting points.
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