Abstract
The reaction of 3-aryl-N-(aryl)propiolamides with arenes in TfOH at room temperature for 0.5 h led to 4,4-diaryl-3,4-dihydroquinolin-2-(1H)-ones in yields of 44–98%. The obtained dihydroquinolinones were further transformed into the corresponding N-acyl or N-formyl derivatives. For the latter, the superelectrophilic activation of the N-formyl group by TfOH in the reaction with benzene resulted in the formation of N-(diphenylmethyl)-substituted dihydroquinolinones.
Highlights
Quinoline derivatives are a very important class of heterocycles, which are used in chemistry, biology, medicine, and materials science
Friedel–Crafts alkenylation of arenes by species A leads to structures 4, which can be diprotonated to the cations B and cyclized to 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones 2
Such 4,4-diaryl-3,4-dihydroquinolin-2-(1H)-ones 2 are very rare objects, there is no general method for their synthesis [16,17]
Summary
Quinoline derivatives are a very important class of heterocycles, which are used in chemistry, biology, medicine, and materials science. The synthesis of quinolines is an important task of organic chemistry [4,5]. Many of these synthetical protocols are based on alkynes, which are widely used for the preparation of various carbo- and heterocycles [6,7,8,9,10]. Based on our works on the synthesis of 4-arylquinolin-2(1H)ones from acetylene compounds under superelectrophilic activation conditions [11,12,13,14], we continued to develop some.
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