JOURNAL ARTICLE

Expanding Synthesizable Space of Disubstituted 1,2,4-Oxadiazoles

Andrey Tolmachev, Andrey V Bogolubsky, Sergey E Pipko, Alexander V Grishchenko, Dmytro V Ushakov, Anton V Zhemera, Oleksandr O Viniychuk, Anzhelika I Konovets, Olga A Zaporozhets, Pavel K Mykhailiuk, Yurii S Moroz
ACS Combinatorial Science 2016 October 10, 18 (10): 616-624
27548754
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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