In the previous decade, there has been an increased focus on molecular three dimensionality in the drug discovery process, due to the observation that drug candidates with a higher mean fraction of sp3 hybridised atoms tend to progress further through the clinical trials process, than compariable “flat” compounds. As a response, there has been a drive in the pharmaceutical industry toward increasing the molecular three dimensionality of screening libraries and discovery molecules. However, bond formation to sp3 hybridised atoms (particularly carbon) represents more of a synthetic challenge than planar or linear counterparts where transition metal catalysed cross coupling methodologies are frequently utilised. One class of inherent three dimensionality compounds are spirocycles and they represent an inviting synthetic target for medicinal chemists due to processing a broad range of biological activity as shown by previous approved pharmaceuticals of this compound class. Herein, we present a procedurally simple, method for the synthesis of spirocyclic dihydropyrazole scaffolds bearing synthetically tractable functional groups to allow a broader range of further synthetic modifications for medicinal chemistry applications.

Synthesis of spirocyclic dihydropyrazoles from tosylhydrazones and electron deficient alkenes

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ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.