Expeditious Construction of Spiro‐Pyrrolidines by an Autocatalytic One‐Pot, Five‐Component, 1,3‐Dipolar Cycloaddition of in situ Generated Azomethine Ylides and Olefinic Dipolarophiles

Abstract

AbstractTwo series of previously unknown spiro‐pyrrolidine derivatives were prepared by a five‐component reaction that employed ninhydrin, 1,2‐phenylenediamine, sarcosine, aldehydes, and malononitrile or cyanoacetic ester in a solvothermal synthesis. This is the first report of an autocatalytic five‐component reaction involving a classical Huisgen reaction, in which the dipole – an azomethine ylide – and the dipolarophile were simultaneously generated in situ. The 1,3‐dipolar cycloaddition reaction was found to proceed in a highly regio‐ and diastereoselective manner. The methodology for the preparation of the spiro‐pyrrolidines could be an ideal tool for green chemistry and the synthesis of alkaloids.