N-Difluorocyclopropyl-Substituted Pyrazoles: Synthesis and Reactivity

Eur. J. Org. Chem. 2019, (27), 4311-4319

DOI: 10.1002/ejoc.201900123

Nosik P.; Poturai A.; Pashko M.; Melnykov K.; Ryabukhin S.; Volochnyuk D.; Grygorenko O.

Difluorocyclopropanation of N‐vinylazoles with the CF3SiMe3–NaI system was studied. It was found that N‐vinylpyrazoles could be transformed into the corresponding N‐difluorocyclopropyl‐substituted derivatives. The method was efficient on a 100 g scale and could be applied for the preparation of various functionalized regioisomeric pyrazole derivatives bearing a gem‐difluorocyclopropane moiety, such as amines, carboxylic acids, aldehydes, bromides, and boronic esters. It was found that N‐difluorocyclopropylpyrazole moiety tolerated many common reagents including nitrating mixture, bromine, aqueous acids and alkali, KMnO4, LiBH4, and Pd0 complexes; it was unstable towards AlCl3, catalytic hydrogenation and lithiation conditions. The products obtained are advanced building blocks which of potential importance to medicinal and agrochemistry.

N-Difluorocyclopropyl-Substituted Pyrazoles: Synthesis and Reactivity


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