2,4‐Bis(fluoroalkyl)quinoline‐3‐carboxylates as Tools for the Development of Potential Agrochemical Ingredients

Abstract

Based on an easy and scalable method for the synthesis of quinoline derivatives substituted by fluorinated groups at both the C‐2 and C‐4 positions developed in our laboratory, we have devised an approach to the synthesis of a new series of unprecedented 2,4‐bis(fluoroalkyl)quinoline‐3‐carboxylates in just two steps. After standard saponification, the latter gave the corresponding 2,4‐bis(fluoroalkyl)quinoline‐3‐carboxylic acids, which served as pivotal intermediates for post‐functionalization reactions. Indeed, the carboxylic group could then be derivatized according to known procedures to introduce chemical diversity at the C‐3 position of these unprecedented structures. The resulting highly functionalized quinolines can serve as a platform for the development of biologically active molecules with strong potential for agrochemical research.

Environmentally Friendly Nafion-Catalyzed Synthesis of Substituted 2-Ethyl-3-Methylquinolines from Aniline and Propionaldehyde under Microwave Irradiation

“…However, only a 30% yield of 3a was observed when liquid Nafion ® NR117 was used as an acid catalyst (entry 16). No better yields were observed by changing the reaction solvents (entries [17][18][19][20]. Changing the heating source from microwave irradiation to normal hot plate, the yield was decreased to 40% yield.…”

“…A quinoline scaffold is a versatile synthetic building block in various natural products [1][2][3][4][5], exceptional pharmaceuticals [6][7][8], physical materials [9][10][11][12][13], and is an important intermediate for asymmetric synthesis [14][15][16][17][18]. Functionalized quinolines are broadly used in agrochemicals [19,20], dyes [21,22], and some biologically active molecules for antimalarial [23][24][25], anticancer [26][27][28][29][30], antiviral [31], antifungal [32], anti-bacterial [33], and anti-inflammatory functions [34,35]. In particular, since the 17th century, the quinoline alkaloid quinine has been viewed historically as the first cure for treating or preventing malaria, [36,37].…”

Regio- and diastereoselective transition metal-free hydroalkylation of N-allenyl sulfonamides by push–pull 2-alkynylquinolines

“…Quinoline scaffolds are one of the most important classes of bioactive heterocyclic aromatic compounds which are broadly embedded in many biological pharmaceuticals, 9 valuable natural products, 10 agrochemical compounds, 11 and industrial processes. 12 A number of drug molecules containing quinoline skeletons such as pitavastatin (cholesterol-lowering agent), 13 saquinavir (anti-retroviral), 14 chloroquine (anti-malarial), 15 mefloquine (anti-malarial), 16 and bedaquiline (anti-TB) 14 are illustrated in Fig.…”

A New Avenue to One-Pot Four-Component Synthesis of Spiro[indoline-3,4′-quinoline] Derivatives Using DABCO as a Green Catalyst

“…9 Or-ganic chemists are more attracted to using DABCO as a catalyst because it is cheap, commercially available, safe, and non-toxic. 10 A while ago, heterocyclic compounds containing quinolone moiety had attracted much more attention of organic chemists due to its various industrial application, 11 for example, in agrochemical, 12 medicine, 13 therapeutic agent, 14 natural product, 15 ligands in transition metal complexes, 16 functional materials, 17 organic light-emitting diodes, 18 electrochemical storage devices, 19 dyes, 20 chemosensors, 21 therapeutic agents, pH indicators, 22 and biological activities. [23][24][25][26][27][28][29] One of the most important quinolone derivatives, that is, spiroindole, is found in many natural products and exhibits many biological activities 30 like antitubercular, 31 antitumor, 32 antimicrobial, 33 antifungal, 34 antimycobacterial, 35 and antioxidant agents, 36 etc.…”