Synthesis of new quinoxaline derivative compounds

Quinoxalines are compounds from the nitrogen-containing heterocyclic compound class, which possess fundamental and pharmacological applications in organic synthesis and medicinal chemistry. Quinoxaline derivatives exhibit numerous bioactivities, especially anti-tumor, antiproliferative, and antineoplastic activity (antimicrobial, antiprotozoal, antiparasitic, antidepressant, anticancer, anti-inflammatory, antituberculosis, antioxidant, antidiabetic, antidepressant, anti-HIV, etc.). Therefore, it is necessary to develop new and effective strategies for the synthesis of substituted quinoxaline compounds. In this thesis study, twelve new quinoxaline derivative compounds (1A–10A, 12A, and 13A) and one compound (11A) synthesized with a different method and in high yield were obtained by reacting 2,3-dichloroquinoxaline (A) with various heterocyclic (nitrogen-containing) ring (piperazine and piperidine derivative) compounds at room temperature in solvent media, and the molecular formulations were confirmed by spectroscopic analysis methods (MS; NMR (¹H; ¹³C); IR). In our experimental studies, new quinoxaline derivative compounds were obtained from the reactions of compound (A), used as the starting material, with 1-(2-furoyl)piperazine (1), 1-piperonylpiperazine (2), 3-hydroxyphenylpiperazine (3), 4-nitrophenylpiperazine (4), 2-cyanophenylpiperazine (5), 4-fluorophenylpiperazine (6), N-allylpiperazine (7), 1-[bis(4-fluorophenyl)methyl]piperazine (8), 1-(2-aminoethyl)piperidine (9), 1-(4-fluorobenzyl)piperazine (10), piperazine (11), 1-amino-4-methylpiperazine (12), and phenylpiperazine (13). From the reaction of 2,3-dichloroquinoxaline (A) with 1-(2-furoyl)piperazine (1), (4-(3-chloroquinoxalin-2-yl)piperazin-1-yl)(furan-2-yl)methanone (1A); with 1-piperonylpiperazine (2), 2-(4-(benzo[d][1,3]dioxol-5-ylmethyl)piperazin-1-yl)-3-chloroquinoxaline (2A) with 3-hydroxyphenylpiperazine (3), 3-(4-(3-chloroquinoxalin-2-yl)piperazin-1-yl)phenol (3A); with 4-nitrophenylpiperazine (4), 2-chloro-3-(4-(4-nitrophenyl)piperazin-1-yl)quinoxaline (4A); with 2-cyanophenylpiperazine (5), 2-(4-(3-chloroquinoxalin-2-yl)piperazin-1-yl)benzonitrile (5A); with 4-fluorophenylpiperazine (6), 2-chloro-3-(4-(4-fluorophenyl)piperazin-1-yl)quinoxaline (6A); with N-allylpiperazine (7), 2-chloro-3-(4-allylpiperazin-1-yl)quinoxaline (7A); with 1-[bis(4-fluorophenyl)methyl]piperazine (8), 2-chloro-3-(1-[bis(4-fluorophenyl)methyl]piperazin-1-yl)quinoxaline (8A); with 1-(2-aminoethyl)piperidine (9), 2-chloro-3-(1-(2-aminoethyl)piperidin-1-yl)quinoxaline (9A); with 1-(4-fluorobenzyl)piperazine (10), 2-chloro-3-(1-(4-fluorobenzyl)piperazin-1-yl)quinoxaline (10A); with piperazine (11), 2-chloro-3-(piperazin-1-yl)quinoxaline (11A); with 1-amino-4-methylpiperazine (12), 2-chloro-3-(1-amino-4-methylpiperazin-1-yl)quinoxaline (12A); with phenylpiperazine (13), 2-chloro-3-(phenylpiperazin-1-yl)quinoxaline (13A) compounds were obtained. As a result of the study, the targeted new quinoxaline derivative compounds were synthesized, and the structural analysis results support their formulations. It is considered that the synthesized new compounds may find applications in a wide range of fields such as pharmacology (antibiotic, antibacterial, antihelminthic, anti-inflammatory, sedative, anticancer, antifungal, antibacterial, antidiabetic, etc.), biomedicine (in the treatment of chronic and metabolic diseases), agriculture (fungicide, herbicide, and insecticide, etc.), material science (electroluminescent materials, fluorescent materials, organic semiconductors, chemically controllable switches, anion receptors, metal corrosion inhibitors, etc.), dyes, and polymers.