Synthesis of some novel imidate derivatives of thiophene and furan: Investigations of their metallation properties and some synthetic applications

RA Barcock, DJ Chadwick, RC Storr, LS Fuller…

Index: Barcock, Richard A.; Chadwick, Derek J.; Storr, Richard C.; Fuller, Lance S.; Young, John H. Tetrahedron, 1994 , vol. 50, # 14 p. 4149 - 4166

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Citation Number: 10

Abstract

Methyl N-methyl-and methyl N-(2, 4, 6-trimethyl) phenyl-2-carboximidates of thiophene and furan have been synthesized in excellent yields by the reaction of sodium methoxide in methanol with the corresponding N-methyl-and N-(2, 4, 6-trimethyl) phenyl-2-carboximidoyl chlorides, which in turn, were obtained from their respective secondary amides by refluxing in neat thionyl chloride. A thorough investigation into the directed lithiation properties of ...