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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Expanding Synthesizable Space of Disubstituted 1,2,4-Oxadiazoles
Andrey Tolmachev1,2, Andrey V Bogolubsky1, Sergey E Pipko2,3
1Enamine Ltd. , 78 Chervonotkatska Street, Kyiv, 02094, Ukraine.
Abstract:
One-pot synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from carboxylic acids and nitriles was optimized to parallel chemistry. The method was validated on a 141 member library; the desired products were recovered with a high success rate and in moderate yields. Practical application of the approach was demonstrated in the synthesis of bioactive compound pifexole and agonists of free fatty acid receptor 1. A library of 4 948 100 synthesizable drug-like 3,5-disubstituted 1,2,4-oxadiazoles was enumerated based on the method and available validated reagents.
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