Synthesis of novel quinolines using TsOH/ionic liquid under microwave

Abstract

Neste trabalho, 3-haloacetil-4-metilquinolinas foram sintetizadas a partir da reação de 4-alcóxi-3-alquen-2-onas [R In this work, 3-haloacetyl-4-methylquinolines were synthesized from the reaction of 4-alkoxy-3-alken-2-ones [R 1 C(O)CH=C(R 2 )OCH 3 , where R 1 = CF 3 , CCl 3 , CHCl 2 , CF 2 Cl, CF 2 CF 3 and R 2 = Me, Et, Pr, Bu, i-Bu and i-Pe] and 2-aminoacetophenone. The reaction was performed in ionic liquid and 4-toluene sulfonic acid under microwave irradiation. Results showed that the catalytic method was effective. Products were formed in a short time (10-20 min) and presented good yields (70-91%).

Synthesis of trifluoromethyl or trifluoroacetyl substituted heterocyclic compounds from trifluoromethyl‐α,β‐ynones

“…[26] However, the synthesis of trifluoroacetylquinolines was rarely reported. [27,28] In 2020 and 2021, a novel and efficient method for synthesis of trifluoromethylpyridines 5 and 7, trifluoromethyl-quinolines 10, or trifluoroacetyl-quinoline derivatives 12 from the reactions of trifluoromethyl-α,β-ynones 3 with β-enamino esters (or ketones) 4, vinyl azides 6, acetanilides 8, anilides, 9 or quinolines 11 in the presence of ZnBr 2 , CuBr 2 /PPh 3 / PMDETA, [RhCp*Cl 2 ] 2 /AgSbF 6 , or morpholine was described by the groups of Hu, Trofimov, Nenajdenko, Wu, Wang, and Cheng (Scheme 3). [10,[29][30][31] The results indicated that the reactions between trifluoromethyl-α,β-ynones 3 and β-enamino esters (or ketones) 4 catalyzed by ZnBr 2 gave 40-82% yields of trifluoromethyl-pyridines 5 except when R 2 in substrates 4 was CF 3 .…”

Microwave‐Assisted Organic Synthesis in Ionic Liquids

“…Prola et al . described the synthesis of novel 3‐haloacylquinolines from 4‐alkoxyvinyl ketones and 2‐aminoacetophenone using TsOH/IL under MW irradiation. It was demonstrated that the synergic effects of ILs and MW operate during the synthesis of quinolines, resulting in short reaction time and good yields.…”

Ionic Liquids-Prompted Synthesis of Biologically Relevant Five- and Six-Membered Heterocyclic Skeletons

“…Martins et al [202] Wang et al [206] also reported a three-component reaction of aryl aldehydes, cyclic β-enaminones, and different active methylene compounds for synthesis of quinolines 116 (Scheme 63) in the presence of [BMIM][BF 4 ] in a molar ratio of 1:52 (reactant/IL). For the series of aldehydes used in these reactions, they found that there was no apparent effect produced from the electronic nature of the aromatic ring substituents.…”

“…The IL was recycled and reused without any loss of activity[202].Srinivasan et al[203] investigated the synthesis of quinolines 112 using the Friedlander heteroannulation tactic by reaction of aminoacetophenones 111 with a variety of ketones or ketoesters in the presence of BBIM and HBIM salts (Scheme 61). (Scheme 60).…”