[4 + 1 + 1] Tandem Cyclization Reaction Involving Isocyanides: Access to 2-(Trifluoromethyl)quinazolin-4(3H)-imines

Abstract

A palladium-catalyzed three-component reaction of isocyanides, 2,2,2-trifluoro-N-(2-iodophenyl)­acetimidoyl chlorides, and amines for the one-pot synthesis of 2-(trifluoromethyl)­quinazolin-4­(3H)-imines was described. The protocol features a wide substrate scope, high efficiency, and readily available raw materials.

Construction of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides and derivatives

“…Very recently, Ji, Xu and co-workers developed a palladium-catalyzed [4+1+1] tandem cyclization reaction of trifuoroacetimidoyl chlorides, isocyanides and amines for the one-pot synthesis of 2-(trifluoromethyl)quinazoline-4(3 H )-imines (Scheme 24). 34 The reaction scope was very broad, as verified that different 2,2,2-trifluoro- N -(2-iodophenyl)acetimidoyl chlorides, isocyanides and amines could be smoothly compatible with the reaction system. Compared with the aforementioned carbonylative work reported by Wu and Chen, 28 isocyanides are usually used as a kind of highly reactive C1 synthons via 1,1-insertion.…”

Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds via trifluoromethyl building blocks

“…In 2022, Ji and co-worker 68 In 2021, Cheng's group 70 synthesized a variety of trifluoromethylimidoyl sulfoxonium ylides (TFISYs) for the first time, and found that these trifluoromethyl building blocks could be used for the preparation of various trifluoromethyl heterocyclics. For example, a lithium-bromide-promoted approach for the preparation of 1,2,3-trisubstituted 5-trifluoromethyl- In 2022, Cheng's group 72 introduced the ruthenium(II)-catalyzed C-H alkylation/amidation of benzoic acids with CF 3imidoyl sulfoxonium ylides, providing an efficient entry to a range of 3-CF 3 isoquinolinones under air conditions (Scheme 55).…”