Sulfonic Acid Functionalized Ionic Liquid in Combinatorial Approach, a Recyclable and Water Tolerant-Acidic Catalyst for One-Pot Friedlander Quinoline Synthesis

Abstract

SO(3)H-functionalized ionic liquid was successfully applied as a water tolerant-acidic catalyst for the one-pot domino approach quinoline synthesis in aqueous medium. Various types of quinolines from 2-aminoaryl ketones and beta-ketoesters/ketones were prepared in 85-98% yields using the catalytic system of SO(3)H-functionalized ionic liquid/H(2)O. The ionic liquids was synthesized in a combinatorial fashion. The quinoline products could be conveniently separated from the reaction mixture by filtration, indicating that the whole process was performed in water and exemplifying a green chemistry. More importantly, the catalyst could be easily recycled for five times without loss of much activity. The catalytic system, reported here, possesses advantages of both homogeneous and heterogeneous catalysts.

Crystal structure of (2-(4-bromophenyl)-5-ethyl-1,3-dioxan-5-yl)methanol, C13H17BrO3

“…These compounds are important for the synthesis of ne chemicals and other industrial applications and have great potential for development [5][6][7]. The crystal structures of some similar 1,3-dioxanes have been reported [8][9][10][11]. The bond lengths and angles are in the expected ranges.…”

Green synthesis of polysubstituted quinoline and benzoquinoline derivatives in ionic liquid via a three-component reaction

“…The crude yellow products were washed with water and purified by 41.1, 50.6, 89.0, 109.7, 119.2, 127.1, 127.5, 128.6, 144.4, 144.7, 148.4, 195.4. IR (KBr): m 3,288, 3,072, 2,962, 2,930, 2,885, 2,811, 2,751, 2,204, 1,659, 1,608, 1,490, 1,469, 1,382, 1,341, 1,319, 1,260, 1,148 m 3,306, 3,226, 3,096, 2,960, 2,880, 2,811, 2,197, 1,657, 1,638, 1,496, 1,434, 1,394, 1,365, 1,316, 1,258, 1,198, 1,166, 1,144, 1,129, 1,067, 1,010 1,660, 1,607, 1,491, 1,470, 1,435, 1,381, 1,316, 1,258, 1,147, 1,020 1,657, 1,609, 1,499, 1,460, 1,434, 1,382, 1,316, 1,257, 1,163, 1,147, 1,138, 1,100, 1 13 1,658, 1,604, 1,501, 1,470, 1,435, 1,381, 1,316, 1,259, 1,148, 1,131, 1,100, 1,045 …”

“…The United States government-sponsored clinical trials for antimalarial drug development showed unequivocally that chloroquine has a significant therapeutic value as an antimalarial drug. Accordingly, novel strategies for the synthesis of quinolines continued to receive considerable attention in the field of organic synthetics chemistry [8][9][10][11][12][13].…”

Green Synthesis of Tetrazines and their Role as Human Cytomegalovirus (HCMV) Protease Inhibitor

“…[5,6]. The easy and efficient route for the synthesis of 1,2,4,5-tetrazines can be done by the addition of hydrazine to aromatic cyanide or aromatic nitriles followed by the oxidation of the 1,2-dihydrotetrazine product [7,8]. Although, this methodology has some demerits like it does not work for producing tetrazines from unactivated nitriles means with alkyl nitriles [9][10][11][12].…”