122818-18-2Relevant articles and documents
N-Difluorocyclopropyl-Substituted Pyrazoles: Synthesis and Reactivity
Nosik, Pavel S.,Poturai, Andrii S.,Pashko, Mykola O.,Melnykov, Kostiantyn P.,Ryabukhin, Sergey V.,Volochnyuk, Dmitriy M.,Grygorenko, Oleksandr O.
, p. 4311 - 4319 (2019/05/15)
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.
