Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 25, Issue 3, Pages 642-647Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.0c00446
Keywords
bicyclo[1.1.1]pentane; bicyclo[1.1.1]pentylpyrazole; bioisostere; [1.1.1]propellane; Chan-Lam coupling; bicyclo[1.1.1]pentylpyrazole hydrazine
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This study presents a novel and scalable method to fill the synthetic gap of generating 1-bicyclo[1.1.1]-pentylpyrazoles, providing a possibility for the production of a host of BCPPs.
The application of bicyclo[1.1.1]pentanes (BCPs) as phenyl bioisosteres has garnered significant attention, as these structural motifs can improve the physiochemical profiles of drug candidates. Despite the potential of using 1-bicyclo[1.1.1]-pentylpyrazoles (BCPPs) as 1-phenylpyrazole bioisosteres, this area remains underexplored because of the relative lack of reliable synthetic methods for the preparation of BCPPs. Herein we address this synthetic gap and report the development of novel and scalable routes to generate a host of BCPPs.
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