4.8 Article

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

Journal

ORGANIC LETTERS
Volume 15, Issue 23, Pages 6094-6097

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol402988s

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Funding

  1. AstraZeneca
  2. EPSRC
  3. EPSRC [EP/J00894X/1] Funding Source: UKRI
  4. Engineering and Physical Sciences Research Council [EP/J00894X/1] Funding Source: researchfish

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Ring-opening of cyclic sulfamidates with propargylic sulfonamides yielded substrates for a gold-catalyzed cyclization to yield tetrahydropyrazines. Manipulation of the tetrahydropyrazines, by reduction or using multicomponent reactions, yielded piperazine scaffolds in which substitution of the carbon atoms was varied. Such scaffolds may have value in the synthesis of novel screening compounds with lead-like molecular properties.

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