Unusual coupling reactions of aldehydes and alkynes: A novel preparation of substituted phthalic acid derivatives by automated synthesis

A Jacobi von Wangelin, H Neumann…

Index: Von Wangelin, Axel Jacobi; Neumann, Helfried; Goerdes, Dirk; Klaus, Stefan; Jiao, Haijun; Spannenberg, Anke; Krueger, Thomas; Wendler, Christian; Thurow, Kerstin; Stoll, Norbert; Beller, Matthias Chemistry - A European Journal, 2003 , vol. 9, # 10 p. 2273 - 2281

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Citation Number: 24

Abstract

Abstract Based upon a highly versatile multicomponent methodology, a new one-pot synthesis of substituted phthalic acid derivatives from α, β-unsaturated aldehydes was developed. The reaction involves the intermediacy of an acetamidodiene species which undergoes Diels–Alder addition to diethyl acetylenedicarboxylate. The resultant acetamidocyclohexadiene is subject to elimination of acetamide under the reaction ...