化学
噻虫啉
哒嗪
组合化学
试剂
氰胺
三氟甲磺酸
吡嗪
胺气处理
苯并呋喃
益达胺
有机化学
催化作用
杀虫剂
农学
生物
噻虫嗪
作者
G. Landelle,Étienne Schmitt,Armen Panossian,Jean‐Pierre Vors,Sergiy Pazenok,Peter Jeschke,Oliver Gutbrod,Frédéric R. Leroux
标识
DOI:10.1016/j.jfluchem.2017.08.006
摘要
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.
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