Copper-Catalyzed Domino Cyclization Reaction Of α-Amino Acid Derivatives And Malononitrile: Synthesis Of Naphthofuran Derivatives

Naphthofuran and its derivatives have been isolated from various natural sources, and have arouse the attention of researchers owing to the fairly wide spectrum of biological and pharmacological activity. Although many methods for the synthesis of naphthofuran derivatives have been developed, most of starting materials are naphthalene derivatives. Even if naphthofuran and its derivatives are accessible by chain compounds, the prevalence of complicated reaction steps, harsh reaction conditions, the low yields and other shortcomings is obvious. Hence, the development of a simple and convenient methodology for the synthesis of naphthafuran derivatives continues to be an important synthetic endeavor in organic chemistry.In this thesis, based on the development of a highly efficient, simple domino reaction, together with a core of achieving simple and efficient cyclization reaction, we mainly studied the copper-catalyzed domino reaction of α-Amino carbonyl compounds and malononitrile in the presence of an oxidant conditions. Details are as follows:A domino cyclization reaction of N-aryl, α′-amino-α,β-unsaturated ketones and malononitrile as carbon nucleophile has been developed and a series of naphthofuran derivatives are obtained in the presence of copper-catalyzed and Ph I(OAc)2. It is obvious that this protocol is associated with concise synthesis route, mild reaction conditions, high atom economy and two rings are created simultaneously in one-pot. Above all, the reaction provides a highly efficient strategy for the direct synthesis of naphthofuran and its derivatives.