Efficient Synthesis of Highly Substituted Furan, Thiophene, Pyrrole and 2-Aminothiazole Derivatives

Author： Metwally Nadia Hanafy  

Publisher： Taylor & Francis Ltd

ISSN： 0039-7911

Source： Synthetic Communications, Vol.37, Iss.23, 2007-01, pp. : 4227-4237

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Abstract

Ethyl cyanoacetate dimer (1) undergoes bromination with N-bromosuccinimide (NBS) to afford 3-amino-4-bromo-2-cyano-pent-2-enedioic acid diethyl ester (2). This bromo derivative reacts with potassium carbonate, sodium hydrogen sulfide, aromatic amines, ammonium thiocyanate, thiourea, N-phenylthiourea, and thiosemicarbazide to afford highly substituted furan, thiophene, pyrrole, and 2-aminothiazole derivatives. Mechanistic explanations as well as structure elucidations are discussed.

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