940895-85-2Relevant articles and documents
Tri- and difluoromethoxylated N-based heterocycles ? Synthesis and insecticidal activity of novel F3CO- and F2HCO-analogues of Imidacloprid and Thiacloprid
Landelle, Gregory,Schmitt, Etienne,Panossian, Armen,Vors, Jean-Pierre,Pazenok, Sergiy,Jeschke, Peter,Gutbrod, Oliver,Leroux, Frédéric R.
, p. 155 - 165 (2017/09/07)
The preparation of F3CO- and F2HCO-analogues of Imidacloprid and Thiacloprid and the evaluation of their biological activity have been performed. For this purpose, a first synthetic approach allowed the preparation of a desired F3CO-containing key intermediate. To allow a facile access to the second F2HCO-containing key intermediate, the difluoromethylation of hydroxylated N-based heterocycles has been developed using difluoromethyl triflate (a liquid non-ODS reagent) under air in aqueous conditions and with very short reaction time. The broad diversity of compatible heterocycles includes a large series of substituted hydroxy-pyridines, but also ?pyrazoles, ?pyrazine, ?pyridazine, and ?quinolines. The couplings of both key intermediates with the required 4,5-dihydro-N-nitro-1H-imidazol-2-amine and [N(Z)]-N-2-thiazolidinylidene-cyanamide were successfully achieved using literature conditions. This work enables the preparation of valuable building blocks, which could lead to the discovery of new bioactive entities.
METHOD FOR THE PREPARATION OF FUNCTIONALIZED TRIHALOMETHOXY SUBSTITUTED PYRIDINES
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Page/Page column 48, (2010/04/28)
The present invention pertains to a process for the preparation of functionalized trihalomethoxypyridines of formula (I) comprising reacting hydroxypyridines with thiophosgene in the presence of a base; reacting the obtained chlorothionoformiates with elemental chlorine and finally converting trichloromethoxy pyridines to trihalomethoxy pyridines using a fluoride source.