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Modular, Gold-Catalyzed Approach to the Synthesis of Lead-like Piperazine Scaffolds

Thomas James, Iain Simpson, J. Andrew Grant, Visuvanathar Sridharan and Adam Nelson*

*School of Chemistry and Astbury Centre for Structural Molecular Biology, University of Leeds, LS2 9JT Leeds, U.K., Email: a.s.nelsonleeds.ac.uk

T. James, I. Simpson, J. Grant, V. Sridharan, A. Nelson, Org. Lett., 2013, 15, 6094-6097.

DOI: 10.1021/ol402988s (free Supporting Information)


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Abstract

Ring-opening of cyclic sulfamidates with propargylic sulfonamides yielded substrates for a gold-catalyzed cyclization to yield tetrahydropyrazines. Subsequent reduction or multicomponent reactions of the tetrahydropyrazines gave various piperazine scaffolds, that have a certain value in the synthesis of novel screening compounds with lead-like molecular properties.

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Key Words

N-Heterocycles, Piperazines


ID: J54-Y2013