Multicomponent reactions are powerful strategies to assemble complex and higher order chemical core structures in a single synthetic transformation. By taking advantage of complexity generating reactions it becomes facile to assemble molecules containing a variety of stereocenters in a cost effective and time-saving manner. Multicomponent reaction sequences followed by a variety of post transformational modifications allows one to synthesize many biologically active molecules that can be readily achieved and also provide a substantial number of derivatives (small molecule libraries). 2-Indolinones and their derivatives have many important functions in biological systems including a wide range of activities. From this perspective, the syntheses of 2-indolinones are interesting targets for organic synthesis and for applications in medicinal chemistry. Our strategy entails the efficient synthesis of 3-substituted 2-indolinones through microwave assistance and selective intramolecular transamidation of the Ugi multi component condensation product(s). Furthermore, investigation of the ability of symmetrical amines versus unsymmetrical amines to eliminate the formation of rotameric mixtures obtained during the process simplifies NMR analysis and allows for further molecular architecture elaboration.

Synthesis of 2-indolinones through microwave-assisted intramolecular transamidation derived from a multicomponent coupling cascade process

249th National Meeting (2015)

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