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The Gewald Synthesis of 2-Aminothiophenes using Activated Sulfur
M. Feroci*, I. Chiarotto, L. Rossi, A. Inesi*
University ”La Sapienza", Rome and Università degli Studi, L’Aquila, Italy
22 January 2009 (online)
Reported is the use of an activated form of sulfur in the classical Gewald synthesis of substituted 2-aminothiophenes from ylidenemalononitriles which are easily obtained from malononitrile and the corresponding ketones. Activation of elemental sulfur was carried out by means of electrogenerated cyanomethyl anion, obtained by galvanostatic reduction from MeCN/Et4NPF6 system. The substrate scope was poorly studied as only two examples were reported involving a different ylidene (R¹ = CONH2 or CO2Et).