3-Trifloxy-3-trifluoromethylpropeniminium Triflate: Reaction with Aromatic Amines – An Efficient Synthesis of 2-Trifluoromethylquinolines

Abstract

The reaction of iminium triflates 2 and 7 with various aromatic amines were investigated. The 2‐Rf‐substituted quinolines 3 and 8 were prepared in excellent yields by the reaction of 2 and 7, respectively, with substituted anilines. The reactions of 2 and 7 with diarylamines proceeds, suprisingly, to afford the corresponding 3‐Rf‐substituted cinnamaldehydes 4 and 9.

Six‐Membered Heterocycles: Quinoline and Isoquinoline

“…A related process is the reaction of anilines with the iminium triflate 35 to yield trifluoromethylquinolines 36 (Scheme 17.8) [46].…”

Ultrasonic-mediated catalyst-free rapid protocol for the multicomponent synthesis of dihydroquinoline derivatives in aqueous media

“…1,4-Dihydroquinoline derivatives have also attracted attention because those comprise a large family of medicinally significant compounds and are used in production of antihypertension, antidiabetic, and many other drugs (12)(13)(14). Due to their widespread biological activity, a number of synthetic strategies have been developed for the preparation of substituted quinolines (15)(16)(17)(18)(19)(20)(21). However, the scarce availability of starting materials, harsh reaction conditions, and the tedious workup procedures are the main drawbacks of many of these methods.…”

One-pot multicomponent synthesis of unsymmetrical polyhydroquinoline derivatives with 1,1′-butylenebispyridinium hydrogen sulfate as an efficient, halogen-free and reusable Brönsted ionic liquid catalyst

“…Nitrogen-containing heterocycles have received much attention in chemistry due to their wide spectrum of pharmacological and biological activities as antiasthmatic, antiinflammatory, antimalarial, anticancer, and anthelmintic agents [20][21][22][23][24][25][26][27][28][29][30]. They are useful dyes and intermediates in organic synthesis [31][32][33][34][35][36][37][38].…”